id sid tid token lemma pos cord-033493-kslzdy8q 1 1 key key JJ cord-033493-kslzdy8q 1 2 : : : cord-033493-kslzdy8q 1 3 cord-033493-kslzdy8q cord-033493-kslzdy8q JJ cord-033493-kslzdy8q 1 4 authors author NNS cord-033493-kslzdy8q 1 5 : : : cord-033493-kslzdy8q 1 6 Hebishy Hebishy NNP cord-033493-kslzdy8q 1 7 , , , cord-033493-kslzdy8q 1 8 Ali Ali NNP cord-033493-kslzdy8q 1 9 M. M. NNP cord-033493-kslzdy8q 1 10 S. S. NNP cord-033493-kslzdy8q 1 11 ; ; : cord-033493-kslzdy8q 1 12 Salama Salama NNP cord-033493-kslzdy8q 1 13 , , , cord-033493-kslzdy8q 1 14 Hagar Hagar NNP cord-033493-kslzdy8q 1 15 T. T. NNP cord-033493-kslzdy8q 1 16 ; ; : cord-033493-kslzdy8q 1 17 Elgemeie Elgemeie NNP cord-033493-kslzdy8q 1 18 , , , cord-033493-kslzdy8q 1 19 Galal Galal NNP cord-033493-kslzdy8q 1 20 H. H. NNP cord-033493-kslzdy8q 1 21 title title NN cord-033493-kslzdy8q 1 22 : : : cord-033493-kslzdy8q 1 23 New New NNP cord-033493-kslzdy8q 1 24 Route Route NNP cord-033493-kslzdy8q 1 25 to to IN cord-033493-kslzdy8q 1 26 the the DT cord-033493-kslzdy8q 1 27 Synthesis Synthesis NNP cord-033493-kslzdy8q 1 28 of of IN cord-033493-kslzdy8q 1 29 Benzamide Benzamide NNP cord-033493-kslzdy8q 1 30 - - HYPH cord-033493-kslzdy8q 1 31 Based base VBN cord-033493-kslzdy8q 1 32 5-Aminopyrazoles 5-aminopyrazoles XX cord-033493-kslzdy8q 2 1 and and CC cord-033493-kslzdy8q 2 2 Their -PRON- PRP$ cord-033493-kslzdy8q 2 3 Fused Fused NNP cord-033493-kslzdy8q 2 4 Heterocycles Heterocycles NNP cord-033493-kslzdy8q 2 5 Showing show VBG cord-033493-kslzdy8q 2 6 Remarkable remarkable JJ cord-033493-kslzdy8q 2 7 Antiavian Antiavian NNP cord-033493-kslzdy8q 2 8 Influenza Influenza NNP cord-033493-kslzdy8q 2 9 Virus Virus NNP cord-033493-kslzdy8q 2 10 Activity Activity NNP cord-033493-kslzdy8q 2 11 date date NN cord-033493-kslzdy8q 2 12 : : : cord-033493-kslzdy8q 2 13 2020 2020 CD cord-033493-kslzdy8q 2 14 - - HYPH cord-033493-kslzdy8q 2 15 09 09 CD cord-033493-kslzdy8q 2 16 - - SYM cord-033493-kslzdy8q 2 17 21 21 CD cord-033493-kslzdy8q 2 18 journal journal NN cord-033493-kslzdy8q 2 19 : : : cord-033493-kslzdy8q 3 1 ACS ACS NNP cord-033493-kslzdy8q 3 2 Omega omega NN cord-033493-kslzdy8q 3 3 DOI DOI NNP cord-033493-kslzdy8q 3 4 : : : cord-033493-kslzdy8q 4 1 10.1021 10.1021 CD cord-033493-kslzdy8q 4 2 / / SYM cord-033493-kslzdy8q 4 3 acsomega.0c02675 acsomega.0c02675 NNP cord-033493-kslzdy8q 4 4 sha sha NNP cord-033493-kslzdy8q 4 5 : : : cord-033493-kslzdy8q 4 6 8707a6182d23f1206c48de6eb272312052944c3e 8707a6182d23f1206c48de6eb272312052944c3e NNP cord-033493-kslzdy8q 4 7 doc_id doc_id CD cord-033493-kslzdy8q 4 8 : : : cord-033493-kslzdy8q 4 9 33493 33493 CD cord-033493-kslzdy8q 4 10 cord_uid cord_uid NNS cord-033493-kslzdy8q 4 11 : : : cord-033493-kslzdy8q 5 1 kslzdy8q kslzdy8q NNP cord-033493-kslzdy8q 6 1 [ [ -LRB- cord-033493-kslzdy8q 6 2 Image image NN cord-033493-kslzdy8q 6 3 : : : cord-033493-kslzdy8q 6 4 see see VB cord-033493-kslzdy8q 6 5 text text NN cord-033493-kslzdy8q 6 6 ] ] -RRB- cord-033493-kslzdy8q 7 1 This this DT cord-033493-kslzdy8q 7 2 study study NN cord-033493-kslzdy8q 7 3 describes describe VBZ cord-033493-kslzdy8q 7 4 a a DT cord-033493-kslzdy8q 7 5 new new JJ cord-033493-kslzdy8q 7 6 route route NN cord-033493-kslzdy8q 7 7 to to IN cord-033493-kslzdy8q 7 8 the the DT cord-033493-kslzdy8q 7 9 synthesis synthesis NN cord-033493-kslzdy8q 7 10 of of IN cord-033493-kslzdy8q 7 11 novel novel JJ cord-033493-kslzdy8q 7 12 benzamide benzamide NN cord-033493-kslzdy8q 7 13 - - HYPH cord-033493-kslzdy8q 7 14 based base VBN cord-033493-kslzdy8q 7 15 5-aminopyrazoles 5-aminopyrazoles CD cord-033493-kslzdy8q 7 16 and and CC cord-033493-kslzdy8q 7 17 their -PRON- PRP$ cord-033493-kslzdy8q 7 18 corresponding correspond VBG cord-033493-kslzdy8q 7 19 pyrazolo[1,5-a]pyrimidine pyrazolo[1,5-a]pyrimidine JJ cord-033493-kslzdy8q 7 20 and and CC cord-033493-kslzdy8q 7 21 pyrazolo[5,1-c][1,2,4]triazine pyrazolo[5,1-c][1,2,4]triazine JJ cord-033493-kslzdy8q 7 22 derivatives derivative NNS cord-033493-kslzdy8q 7 23 . . . cord-033493-kslzdy8q 8 1 Benzamide Benzamide NNP cord-033493-kslzdy8q 8 2 - - HYPH cord-033493-kslzdy8q 8 3 based base VBN cord-033493-kslzdy8q 8 4 5-aminopyrazoles 5-aminopyrazoles CD cord-033493-kslzdy8q 8 5 were be VBD cord-033493-kslzdy8q 8 6 prepared prepare VBN cord-033493-kslzdy8q 8 7 through through IN cord-033493-kslzdy8q 8 8 a a DT cord-033493-kslzdy8q 8 9 reaction reaction NN cord-033493-kslzdy8q 8 10 of of IN cord-033493-kslzdy8q 8 11 benzoyl benzoyl NN cord-033493-kslzdy8q 8 12 isothiocyanate isothiocyanate NN cord-033493-kslzdy8q 8 13 with with IN cord-033493-kslzdy8q 8 14 malononitrile malononitrile NN cord-033493-kslzdy8q 8 15 in in IN cord-033493-kslzdy8q 8 16 KOH KOH NNP cord-033493-kslzdy8q 8 17 – – : cord-033493-kslzdy8q 8 18 EtOH EtOH NNP cord-033493-kslzdy8q 8 19 followed follow VBD cord-033493-kslzdy8q 8 20 by by IN cord-033493-kslzdy8q 8 21 alkylation alkylation NN cord-033493-kslzdy8q 8 22 with with IN cord-033493-kslzdy8q 8 23 alkyl alkyl JJ cord-033493-kslzdy8q 8 24 halides halide NNS cord-033493-kslzdy8q 8 25 and and CC cord-033493-kslzdy8q 8 26 then then RB cord-033493-kslzdy8q 8 27 a a DT cord-033493-kslzdy8q 8 28 reaction reaction NN cord-033493-kslzdy8q 8 29 with with IN cord-033493-kslzdy8q 8 30 hydrazine hydrazine NN cord-033493-kslzdy8q 8 31 . . . cord-033493-kslzdy8q 9 1 In in IN cord-033493-kslzdy8q 9 2 an an DT cord-033493-kslzdy8q 9 3 attempt attempt NN cord-033493-kslzdy8q 9 4 to to TO cord-033493-kslzdy8q 9 5 react react VB cord-033493-kslzdy8q 9 6 benzoyl benzoyl NN cord-033493-kslzdy8q 9 7 isothiocyanate isothiocyanate NN cord-033493-kslzdy8q 9 8 with with IN cord-033493-kslzdy8q 9 9 ethyl ethyl NN cord-033493-kslzdy8q 9 10 cyanoacetate cyanoacetate NN cord-033493-kslzdy8q 9 11 in in IN cord-033493-kslzdy8q 9 12 KOH KOH NNP cord-033493-kslzdy8q 9 13 – – : cord-033493-kslzdy8q 9 14 EtOH EtOH NNP cord-033493-kslzdy8q 9 15 followed follow VBD cord-033493-kslzdy8q 9 16 by by IN cord-033493-kslzdy8q 9 17 alkylation alkylation NN cord-033493-kslzdy8q 9 18 with with IN cord-033493-kslzdy8q 9 19 methyl methyl NN cord-033493-kslzdy8q 9 20 iodide iodide NN cord-033493-kslzdy8q 9 21 at at IN cord-033493-kslzdy8q 9 22 room room NN cord-033493-kslzdy8q 9 23 temperature temperature NN cord-033493-kslzdy8q 9 24 and and CC cord-033493-kslzdy8q 9 25 then then RB cord-033493-kslzdy8q 9 26 a a DT cord-033493-kslzdy8q 9 27 reaction reaction NN cord-033493-kslzdy8q 9 28 with with IN cord-033493-kslzdy8q 9 29 hydrazine hydrazine NN cord-033493-kslzdy8q 9 30 has have VBZ cord-033493-kslzdy8q 9 31 resulted result VBN cord-033493-kslzdy8q 9 32 in in IN cord-033493-kslzdy8q 9 33 the the DT cord-033493-kslzdy8q 9 34 formation formation NN cord-033493-kslzdy8q 9 35 of of IN cord-033493-kslzdy8q 9 36 3-ethoxy-5-phenyl-1H-1,2,4-triazole 3-ethoxy-5-phenyl-1h-1,2,4-triazole CD cord-033493-kslzdy8q 9 37 . . . cord-033493-kslzdy8q 10 1 The the DT cord-033493-kslzdy8q 10 2 structures structure NNS cord-033493-kslzdy8q 10 3 of of IN cord-033493-kslzdy8q 10 4 the the DT cord-033493-kslzdy8q 10 5 new new JJ cord-033493-kslzdy8q 10 6 compounds compound NNS cord-033493-kslzdy8q 10 7 were be VBD cord-033493-kslzdy8q 10 8 characterized characterize VBN cord-033493-kslzdy8q 10 9 by by IN cord-033493-kslzdy8q 10 10 mass mass NN cord-033493-kslzdy8q 10 11 spectroscopy spectroscopy NN cord-033493-kslzdy8q 10 12 , , , cord-033493-kslzdy8q 10 13 ( ( -LRB- cord-033493-kslzdy8q 10 14 1)H 1)h CD cord-033493-kslzdy8q 10 15 nuclear nuclear JJ cord-033493-kslzdy8q 10 16 magnetic magnetic JJ cord-033493-kslzdy8q 10 17 resonance resonance NN cord-033493-kslzdy8q 10 18 ( ( -LRB- cord-033493-kslzdy8q 10 19 ( ( -LRB- cord-033493-kslzdy8q 10 20 1)H 1)h CD cord-033493-kslzdy8q 10 21 NMR NMR NNP cord-033493-kslzdy8q 10 22 ) ) -RRB- cord-033493-kslzdy8q 10 23 spectroscopy spectroscopy NN cord-033493-kslzdy8q 10 24 , , , cord-033493-kslzdy8q 10 25 infrared infrared JJ cord-033493-kslzdy8q 10 26 spectroscopy spectroscopy NN cord-033493-kslzdy8q 10 27 ( ( -LRB- cord-033493-kslzdy8q 10 28 IR IR NNP cord-033493-kslzdy8q 10 29 ) ) -RRB- cord-033493-kslzdy8q 10 30 , , , cord-033493-kslzdy8q 10 31 and and CC cord-033493-kslzdy8q 10 32 X x NN cord-033493-kslzdy8q 10 33 - - NN cord-033493-kslzdy8q 10 34 ray ray JJ cord-033493-kslzdy8q 10 35 analysis analysis NN cord-033493-kslzdy8q 10 36 . . . cord-033493-kslzdy8q 11 1 The the DT cord-033493-kslzdy8q 11 2 new new JJ cord-033493-kslzdy8q 11 3 compounds compound NNS cord-033493-kslzdy8q 11 4 were be VBD cord-033493-kslzdy8q 11 5 tested test VBN cord-033493-kslzdy8q 11 6 in in IN cord-033493-kslzdy8q 11 7 vitro vitro FW cord-033493-kslzdy8q 11 8 for for IN cord-033493-kslzdy8q 11 9 their -PRON- PRP$ cord-033493-kslzdy8q 11 10 anti anti JJ cord-033493-kslzdy8q 11 11 - - JJ cord-033493-kslzdy8q 11 12 influenza influenza JJ cord-033493-kslzdy8q 11 13 A a DT cord-033493-kslzdy8q 11 14 virus virus NN cord-033493-kslzdy8q 11 15 ( ( -LRB- cord-033493-kslzdy8q 11 16 subtype subtype NN cord-033493-kslzdy8q 11 17 H5N1 H5N1 NNP cord-033493-kslzdy8q 11 18 ) ) -RRB- cord-033493-kslzdy8q 11 19 activity activity NN cord-033493-kslzdy8q 11 20 . . . cord-033493-kslzdy8q 12 1 Among among IN cord-033493-kslzdy8q 12 2 the the DT cord-033493-kslzdy8q 12 3 synthesized synthesize VBN cord-033493-kslzdy8q 12 4 compounds compound NNS cord-033493-kslzdy8q 12 5 , , , cord-033493-kslzdy8q 12 6 eight eight CD cord-033493-kslzdy8q 12 7 compounds compound NNS cord-033493-kslzdy8q 12 8 3b 3b CD cord-033493-kslzdy8q 12 9 , , , cord-033493-kslzdy8q 12 10 4 4 CD cord-033493-kslzdy8q 12 11 , , , cord-033493-kslzdy8q 12 12 10b 10b NNS cord-033493-kslzdy8q 12 13 , , , cord-033493-kslzdy8q 12 14 10c 10c CD cord-033493-kslzdy8q 12 15 , , , cord-033493-kslzdy8q 12 16 12a 12a NNS cord-033493-kslzdy8q 12 17 , , , cord-033493-kslzdy8q 12 18 19 19 CD cord-033493-kslzdy8q 12 19 , , , cord-033493-kslzdy8q 12 20 21a 21a NNS cord-033493-kslzdy8q 12 21 , , , cord-033493-kslzdy8q 12 22 and and CC cord-033493-kslzdy8q 12 23 21b 21b NNS cord-033493-kslzdy8q 12 24 were be VBD cord-033493-kslzdy8q 12 25 found find VBN cord-033493-kslzdy8q 12 26 to to TO cord-033493-kslzdy8q 12 27 possess possess VB cord-033493-kslzdy8q 12 28 significant significant JJ cord-033493-kslzdy8q 12 29 antiviral antiviral JJ cord-033493-kslzdy8q 12 30 activities activity NNS cord-033493-kslzdy8q 12 31 against against IN cord-033493-kslzdy8q 12 32 bird bird NN cord-033493-kslzdy8q 12 33 flu flu NN cord-033493-kslzdy8q 12 34 influenza influenza NN cord-033493-kslzdy8q 12 35 ( ( -LRB- cord-033493-kslzdy8q 12 36 H5N1 H5N1 NNP cord-033493-kslzdy8q 12 37 ) ) -RRB- cord-033493-kslzdy8q 12 38 with with IN cord-033493-kslzdy8q 12 39 viral viral JJ cord-033493-kslzdy8q 12 40 reduction reduction NN cord-033493-kslzdy8q 12 41 in in IN cord-033493-kslzdy8q 12 42 the the DT cord-033493-kslzdy8q 12 43 range range NN cord-033493-kslzdy8q 12 44 of of IN cord-033493-kslzdy8q 12 45 85–65 85–65 CD cord-033493-kslzdy8q 12 46 % % NN cord-033493-kslzdy8q 12 47 . . . cord-033493-kslzdy8q 13 1 The the DT cord-033493-kslzdy8q 13 2 emergence emergence NN cord-033493-kslzdy8q 13 3 of of IN cord-033493-kslzdy8q 13 4 bird bird NN cord-033493-kslzdy8q 13 5 flu flu NN cord-033493-kslzdy8q 13 6 virus virus NN cord-033493-kslzdy8q 13 7 ( ( -LRB- cord-033493-kslzdy8q 13 8 H5N1 H5N1 NNP cord-033493-kslzdy8q 13 9 ) ) -RRB- cord-033493-kslzdy8q 13 10 23 23 CD cord-033493-kslzdy8q 13 11 years year NNS cord-033493-kslzdy8q 13 12 ago ago RB cord-033493-kslzdy8q 13 13 has have VBZ cord-033493-kslzdy8q 13 14 caused cause VBN cord-033493-kslzdy8q 13 15 several several JJ cord-033493-kslzdy8q 13 16 diseases disease NNS cord-033493-kslzdy8q 13 17 in in IN cord-033493-kslzdy8q 13 18 mankind mankind NN cord-033493-kslzdy8q 13 19 over over IN cord-033493-kslzdy8q 13 20 the the DT cord-033493-kslzdy8q 13 21 past past JJ cord-033493-kslzdy8q 13 22 few few JJ cord-033493-kslzdy8q 13 23 years year NNS cord-033493-kslzdy8q 13 24 , , , cord-033493-kslzdy8q 13 25 and and CC cord-033493-kslzdy8q 13 26 now now RB cord-033493-kslzdy8q 13 27 , , , cord-033493-kslzdy8q 13 28 it -PRON- PRP cord-033493-kslzdy8q 13 29 is be VBZ cord-033493-kslzdy8q 13 30 spreading spread VBG cord-033493-kslzdy8q 13 31 in in IN cord-033493-kslzdy8q 13 32 the the DT cord-033493-kslzdy8q 13 33 world world NN cord-033493-kslzdy8q 13 34 a a DT cord-033493-kslzdy8q 13 35 very very RB cord-033493-kslzdy8q 13 36 deadly deadly JJ cord-033493-kslzdy8q 13 37 influenza influenza NN cord-033493-kslzdy8q 13 38 pandemic pandemic NN cord-033493-kslzdy8q 13 39 , , , cord-033493-kslzdy8q 13 40 which which WDT cord-033493-kslzdy8q 13 41 is be VBZ cord-033493-kslzdy8q 13 42 Covid-19 Covid-19 NNP cord-033493-kslzdy8q 13 43 and and CC cord-033493-kslzdy8q 13 44 has have VBZ cord-033493-kslzdy8q 13 45 caused cause VBN cord-033493-kslzdy8q 13 46 the the DT cord-033493-kslzdy8q 13 47 death death NN cord-033493-kslzdy8q 13 48 of of IN cord-033493-kslzdy8q 13 49 many many JJ cord-033493-kslzdy8q 13 50 people people NNS cord-033493-kslzdy8q 13 51 . . . cord-033493-kslzdy8q 14 1 We -PRON- PRP cord-033493-kslzdy8q 14 2 had have VBD cord-033493-kslzdy8q 14 3 to to TO cord-033493-kslzdy8q 14 4 put put VB cord-033493-kslzdy8q 14 5 in in IN cord-033493-kslzdy8q 14 6 place place NN cord-033493-kslzdy8q 14 7 several several JJ cord-033493-kslzdy8q 14 8 measures measure NNS cord-033493-kslzdy8q 14 9 to to TO cord-033493-kslzdy8q 14 10 prevent prevent VB cord-033493-kslzdy8q 14 11 the the DT cord-033493-kslzdy8q 14 12 spread spread NN cord-033493-kslzdy8q 14 13 of of IN cord-033493-kslzdy8q 14 14 these these DT cord-033493-kslzdy8q 14 15 influenza influenza NN cord-033493-kslzdy8q 14 16 viruses virus NNS cord-033493-kslzdy8q 14 17 by by IN cord-033493-kslzdy8q 14 18 developing develop VBG cord-033493-kslzdy8q 14 19 pharmaceutical pharmaceutical JJ cord-033493-kslzdy8q 14 20 strategies strategy NNS cord-033493-kslzdy8q 14 21 to to TO cord-033493-kslzdy8q 14 22 design design VB cord-033493-kslzdy8q 14 23 drugs drug NNS cord-033493-kslzdy8q 14 24 for for IN cord-033493-kslzdy8q 14 25 combating combat VBG cord-033493-kslzdy8q 14 26 influenza influenza NN cord-033493-kslzdy8q 14 27 viruses virus NNS cord-033493-kslzdy8q 14 28 of of IN cord-033493-kslzdy8q 14 29 all all DT cord-033493-kslzdy8q 14 30 kinds kind NNS cord-033493-kslzdy8q 14 31 . . . cord-033493-kslzdy8q 15 1 5-Aminopyrazoles 5-Aminopyrazoles NNP cord-033493-kslzdy8q 15 2 and and CC cord-033493-kslzdy8q 15 3 their -PRON- PRP$ cord-033493-kslzdy8q 15 4 fused fuse VBN cord-033493-kslzdy8q 15 5 triazine triazine NNP cord-033493-kslzdy8q 15 6 and and CC cord-033493-kslzdy8q 15 7 pyrimidine pyrimidine NN cord-033493-kslzdy8q 15 8 ring ring NN cord-033493-kslzdy8q 15 9 systems system NNS cord-033493-kslzdy8q 15 10 are be VBP cord-033493-kslzdy8q 15 11 analogs analog NNS cord-033493-kslzdy8q 15 12 of of IN cord-033493-kslzdy8q 15 13 purines purine NNS cord-033493-kslzdy8q 15 14 and and CC cord-033493-kslzdy8q 15 15 thioguanines thioguanines NNP cord-033493-kslzdy8q 15 16 , , , cord-033493-kslzdy8q 15 17 which which WDT cord-033493-kslzdy8q 15 18 are be VBP cord-033493-kslzdy8q 15 19 the the DT cord-033493-kslzdy8q 15 20 mostly mostly RB cord-033493-kslzdy8q 15 21 used use VBN cord-033493-kslzdy8q 15 22 antimetabolic antimetabolic JJ cord-033493-kslzdy8q 15 23 agents agent NNS cord-033493-kslzdy8q 15 24 . . . cord-033493-kslzdy8q 16 1 Pyrazoles pyrazole NNS cord-033493-kslzdy8q 16 2 share share VBP cord-033493-kslzdy8q 16 3 their -PRON- PRP$ cord-033493-kslzdy8q 16 4 structural structural JJ cord-033493-kslzdy8q 16 5 design design NN cord-033493-kslzdy8q 16 6 with with IN cord-033493-kslzdy8q 16 7 several several JJ cord-033493-kslzdy8q 16 8 drugs drug NNS cord-033493-kslzdy8q 16 9 , , , cord-033493-kslzdy8q 16 10 and and CC cord-033493-kslzdy8q 16 11 biologically biologically RB cord-033493-kslzdy8q 16 12 dynamic dynamic JJ cord-033493-kslzdy8q 16 13 compounds compound NNS cord-033493-kslzdy8q 16 14 exhibit exhibit VBP cord-033493-kslzdy8q 16 15 activities activity NNS cord-033493-kslzdy8q 16 16 such such JJ cord-033493-kslzdy8q 16 17 as as IN cord-033493-kslzdy8q 16 18 anti anti JJ cord-033493-kslzdy8q 16 19 - - JJ cord-033493-kslzdy8q 16 20 inflammatory inflammatory JJ cord-033493-kslzdy8q 16 21 , , , cord-033493-kslzdy8q 16 22 anticancer anticancer JJ cord-033493-kslzdy8q 16 23 , , , cord-033493-kslzdy8q 16 24 and and CC cord-033493-kslzdy8q 16 25 antihypertensive antihypertensive NN cord-033493-kslzdy8q 16 26 . . . cord-033493-kslzdy8q 17 1 1−3 1−3 CD cord-033493-kslzdy8q 18 1 Our -PRON- PRP$ cord-033493-kslzdy8q 18 2 group group NN cord-033493-kslzdy8q 18 3 has have VBZ cord-033493-kslzdy8q 18 4 actively actively RB cord-033493-kslzdy8q 18 5 embarked embark VBN cord-033493-kslzdy8q 18 6 on on IN cord-033493-kslzdy8q 18 7 a a DT cord-033493-kslzdy8q 18 8 program program NN cord-033493-kslzdy8q 18 9 for for IN cord-033493-kslzdy8q 18 10 the the DT cord-033493-kslzdy8q 18 11 development development NN cord-033493-kslzdy8q 18 12 of of IN cord-033493-kslzdy8q 18 13 new new JJ cord-033493-kslzdy8q 18 14 methods method NNS cord-033493-kslzdy8q 18 15 for for IN cord-033493-kslzdy8q 18 16 the the DT cord-033493-kslzdy8q 18 17 synthesis synthesis NN cord-033493-kslzdy8q 18 18 of of IN cord-033493-kslzdy8q 18 19 5-aminopyrazoles 5-aminopyrazoles CD cord-033493-kslzdy8q 18 20 as as IN cord-033493-kslzdy8q 18 21 potential potential JJ cord-033493-kslzdy8q 18 22 bioactive bioactive JJ cord-033493-kslzdy8q 18 23 agents agent NNS cord-033493-kslzdy8q 18 24 . . . cord-033493-kslzdy8q 19 1 4,5 4,5 LS cord-033493-kslzdy8q 19 2 5-Aminoyrazoles 5-aminoyrazoles CD cord-033493-kslzdy8q 19 3 have have VBP cord-033493-kslzdy8q 19 4 been be VBN cord-033493-kslzdy8q 19 5 used use VBN cord-033493-kslzdy8q 19 6 to to TO cord-033493-kslzdy8q 19 7 synthesize synthesize VB cord-033493-kslzdy8q 19 8 numerous numerous JJ cord-033493-kslzdy8q 19 9 other other JJ cord-033493-kslzdy8q 19 10 fused fuse VBN cord-033493-kslzdy8q 19 11 heterocycles heterocycle NNS cord-033493-kslzdy8q 19 12 . . . cord-033493-kslzdy8q 20 1 Pyrazolo Pyrazolo NNP cord-033493-kslzdy8q 20 2 [ [ -LRB- cord-033493-kslzdy8q 20 3 1,5-a 1,5-a CD cord-033493-kslzdy8q 20 4 ] ] -RRB- cord-033493-kslzdy8q 20 5 pyrimidines pyrimidine NNS cord-033493-kslzdy8q 20 6 , , , cord-033493-kslzdy8q 20 7 in in IN cord-033493-kslzdy8q 20 8 particular particular JJ cord-033493-kslzdy8q 20 9 , , , cord-033493-kslzdy8q 20 10 have have VBP cord-033493-kslzdy8q 20 11 shown show VBN cord-033493-kslzdy8q 20 12 valuable valuable JJ cord-033493-kslzdy8q 20 13 pharmaceutical pharmaceutical NN cord-033493-kslzdy8q 20 14 uses use NNS cord-033493-kslzdy8q 20 15 including include VBG cord-033493-kslzdy8q 20 16 various various JJ cord-033493-kslzdy8q 20 17 antiviral antiviral JJ cord-033493-kslzdy8q 20 18 , , , cord-033493-kslzdy8q 20 19 antimicrobial antimicrobial JJ cord-033493-kslzdy8q 20 20 , , , cord-033493-kslzdy8q 20 21 and and CC cord-033493-kslzdy8q 20 22 antitumor antitumor JJ cord-033493-kslzdy8q 20 23 activities activity NNS cord-033493-kslzdy8q 20 24 . . . cord-033493-kslzdy8q 21 1 6−11 6−11 CD cord-033493-kslzdy8q 22 1 Some some DT cord-033493-kslzdy8q 22 2 compounds compound NNS cord-033493-kslzdy8q 22 3 comprising comprise VBG cord-033493-kslzdy8q 22 4 this this DT cord-033493-kslzdy8q 22 5 scaffold scaffold NN cord-033493-kslzdy8q 22 6 are be VBP cord-033493-kslzdy8q 22 7 official official JJ cord-033493-kslzdy8q 22 8 and and CC cord-033493-kslzdy8q 22 9 commercialized commercialize VBN cord-033493-kslzdy8q 22 10 drugs drug NNS cord-033493-kslzdy8q 22 11 , , , cord-033493-kslzdy8q 22 12 for for IN cord-033493-kslzdy8q 22 13 example example NN cord-033493-kslzdy8q 22 14 , , , cord-033493-kslzdy8q 22 15 zaleplon zaleplon NNP cord-033493-kslzdy8q 22 16 ( ( -LRB- cord-033493-kslzdy8q 22 17 A A NNP cord-033493-kslzdy8q 22 18 ) ) -RRB- cord-033493-kslzdy8q 22 19 , , , cord-033493-kslzdy8q 22 20 lorediplon lorediplon NNP cord-033493-kslzdy8q 22 21 ( ( -LRB- cord-033493-kslzdy8q 22 22 B B NNP cord-033493-kslzdy8q 22 23 ) ) -RRB- cord-033493-kslzdy8q 22 24 , , , cord-033493-kslzdy8q 22 25 indiplon indiplon NNP cord-033493-kslzdy8q 22 26 ( ( -LRB- cord-033493-kslzdy8q 22 27 C C NNP cord-033493-kslzdy8q 22 28 ) ) -RRB- cord-033493-kslzdy8q 22 29 , , , cord-033493-kslzdy8q 22 30 anagliptin anagliptin NNP cord-033493-kslzdy8q 22 31 ( ( -LRB- cord-033493-kslzdy8q 22 32 D D NNP cord-033493-kslzdy8q 22 33 ) ) -RRB- cord-033493-kslzdy8q 22 34 , , , cord-033493-kslzdy8q 22 35 and and CC cord-033493-kslzdy8q 22 36 ocinaplon ocinaplon JJ cord-033493-kslzdy8q 22 37 ( ( -LRB- cord-033493-kslzdy8q 22 38 E e NN cord-033493-kslzdy8q 22 39 ) ) -RRB- cord-033493-kslzdy8q 22 40 ( ( -LRB- cord-033493-kslzdy8q 22 41 Figure figure NN cord-033493-kslzdy8q 22 42 1 1 CD cord-033493-kslzdy8q 22 43 ) ) -RRB- cord-033493-kslzdy8q 22 44 . . . cord-033493-kslzdy8q 23 1 We -PRON- PRP cord-033493-kslzdy8q 23 2 have have VBP cord-033493-kslzdy8q 23 3 recently recently RB cord-033493-kslzdy8q 23 4 reported report VBN cord-033493-kslzdy8q 23 5 different different JJ cord-033493-kslzdy8q 23 6 successful successful JJ cord-033493-kslzdy8q 23 7 synthetic synthetic JJ cord-033493-kslzdy8q 23 8 methods method NNS cord-033493-kslzdy8q 23 9 to to TO cord-033493-kslzdy8q 23 10 prepare prepare VB cord-033493-kslzdy8q 23 11 pyrazolo pyrazolo NNP cord-033493-kslzdy8q 23 12 [ [ -LRB- cord-033493-kslzdy8q 23 13 1,5-a 1,5-a CD cord-033493-kslzdy8q 23 14 ] ] -RRB- cord-033493-kslzdy8q 23 15 pyrimidines pyrimidine NNS cord-033493-kslzdy8q 23 16 , , , cord-033493-kslzdy8q 23 17 which which WDT cord-033493-kslzdy8q 23 18 found find VBD cord-033493-kslzdy8q 23 19 application application NN cord-033493-kslzdy8q 23 20 and and CC cord-033493-kslzdy8q 23 21 appear appear VBP cord-033493-kslzdy8q 23 22 to to TO cord-033493-kslzdy8q 23 23 constitute constitute VB cord-033493-kslzdy8q 23 24 new new JJ cord-033493-kslzdy8q 23 25 classes class NNS cord-033493-kslzdy8q 23 26 of of IN cord-033493-kslzdy8q 23 27 antimetabolic antimetabolic JJ cord-033493-kslzdy8q 23 28 agents agent NNS cord-033493-kslzdy8q 23 29 . . . cord-033493-kslzdy8q 24 1 12−15 12−15 LS cord-033493-kslzdy8q 24 2 Pyrazolo Pyrazolo NNP cord-033493-kslzdy8q 24 3 [ [ -LRB- cord-033493-kslzdy8q 24 4 5,1-c 5,1-c CD cord-033493-kslzdy8q 24 5 ] ] -RRB- cord-033493-kslzdy8q 24 6 triazines triazine NNS cord-033493-kslzdy8q 24 7 Synthesis Synthesis NNP cord-033493-kslzdy8q 24 8 of of IN cord-033493-kslzdy8q 24 9 3-ethoxy-5-phenyl 3-ethoxy-5-phenyl CD cord-033493-kslzdy8q 24 10 include include VBP cord-033493-kslzdy8q 24 11 a a DT cord-033493-kslzdy8q 24 12 large large JJ cord-033493-kslzdy8q 24 13 number number NN cord-033493-kslzdy8q 24 14 of of IN cord-033493-kslzdy8q 24 15 compounds compound NNS cord-033493-kslzdy8q 24 16 with with IN cord-033493-kslzdy8q 24 17 broad broad JJ cord-033493-kslzdy8q 24 18 biological biological JJ cord-033493-kslzdy8q 24 19 activities activity NNS cord-033493-kslzdy8q 24 20 . . . cord-033493-kslzdy8q 25 1 The the DT cord-033493-kslzdy8q 25 2 pyrazolo pyrazolo NN cord-033493-kslzdy8q 25 3 [ [ -LRB- cord-033493-kslzdy8q 25 4 5,1-c 5,1-c CD cord-033493-kslzdy8q 25 5 ] ] -RRB- cord-033493-kslzdy8q 25 6 triazines triazine NNS cord-033493-kslzdy8q 25 7 are be VBP cord-033493-kslzdy8q 25 8 well well RB cord-033493-kslzdy8q 25 9 known know VBN cord-033493-kslzdy8q 25 10 as as IN cord-033493-kslzdy8q 25 11 the the DT cord-033493-kslzdy8q 25 12 most most RBS cord-033493-kslzdy8q 25 13 potent potent JJ cord-033493-kslzdy8q 25 14 scaffold scaffold NN cord-033493-kslzdy8q 25 15 for for IN cord-033493-kslzdy8q 25 16 synthesizing synthesize VBG cord-033493-kslzdy8q 25 17 potential potential JJ cord-033493-kslzdy8q 25 18 therapeutics therapeutic NNS cord-033493-kslzdy8q 25 19 . . . cord-033493-kslzdy8q 26 1 The the DT cord-033493-kslzdy8q 26 2 applications application NNS cord-033493-kslzdy8q 26 3 of of IN cord-033493-kslzdy8q 26 4 these these DT cord-033493-kslzdy8q 26 5 ring ring NN cord-033493-kslzdy8q 26 6 systems system NNS cord-033493-kslzdy8q 26 7 as as IN cord-033493-kslzdy8q 26 8 kinase kinase NN cord-033493-kslzdy8q 26 9 inhibitors inhibitor NNS cord-033493-kslzdy8q 26 10 are be VBP cord-033493-kslzdy8q 26 11 growing grow VBG cord-033493-kslzdy8q 26 12 and and CC cord-033493-kslzdy8q 26 13 are be VBP cord-033493-kslzdy8q 26 14 very very RB cord-033493-kslzdy8q 26 15 successful successful JJ cord-033493-kslzdy8q 26 16 in in IN cord-033493-kslzdy8q 26 17 the the DT cord-033493-kslzdy8q 26 18 last last JJ cord-033493-kslzdy8q 26 19 few few JJ cord-033493-kslzdy8q 26 20 years year NNS cord-033493-kslzdy8q 26 21 . . . cord-033493-kslzdy8q 27 1 16−19 16−19 LS cord-033493-kslzdy8q 27 2 We -PRON- PRP cord-033493-kslzdy8q 27 3 have have VBP cord-033493-kslzdy8q 27 4 recently recently RB cord-033493-kslzdy8q 27 5 reported report VBN cord-033493-kslzdy8q 27 6 different different JJ cord-033493-kslzdy8q 27 7 successful successful JJ cord-033493-kslzdy8q 27 8 synthetic synthetic JJ cord-033493-kslzdy8q 27 9 methods method NNS cord-033493-kslzdy8q 27 10 to to TO cord-033493-kslzdy8q 27 11 prepare prepare VB cord-033493-kslzdy8q 27 12 pyrazolotriazines pyrazolotriazine NNS cord-033493-kslzdy8q 27 13 , , , cord-033493-kslzdy8q 27 14 which which WDT cord-033493-kslzdy8q 27 15 found find VBD cord-033493-kslzdy8q 27 16 application application NN cord-033493-kslzdy8q 27 17 and and CC cord-033493-kslzdy8q 27 18 appear appear VBP cord-033493-kslzdy8q 27 19 to to TO cord-033493-kslzdy8q 27 20 constitute constitute VB cord-033493-kslzdy8q 27 21 new new JJ cord-033493-kslzdy8q 27 22 classes class NNS cord-033493-kslzdy8q 27 23 of of IN cord-033493-kslzdy8q 27 24 antimetabolic antimetabolic JJ cord-033493-kslzdy8q 27 25 agents agent NNS cord-033493-kslzdy8q 27 26 . . . cord-033493-kslzdy8q 28 1 20 20 CD cord-033493-kslzdy8q 28 2 , , , cord-033493-kslzdy8q 28 3 21 21 CD cord-033493-kslzdy8q 28 4 One one CD cord-033493-kslzdy8q 28 5 of of IN cord-033493-kslzdy8q 28 6 our -PRON- PRP$ cord-033493-kslzdy8q 28 7 previously previously RB cord-033493-kslzdy8q 28 8 reported report VBN cord-033493-kslzdy8q 28 9 series series NN cord-033493-kslzdy8q 28 10 of of IN cord-033493-kslzdy8q 28 11 novel novel JJ cord-033493-kslzdy8q 28 12 5-aminopyrazoles 5-aminopyrazoles CD cord-033493-kslzdy8q 28 13 F F NNP cord-033493-kslzdy8q 28 14 and and CC cord-033493-kslzdy8q 28 15 G G NNP cord-033493-kslzdy8q 28 16 ( ( -LRB- cord-033493-kslzdy8q 28 17 Figure figure NN cord-033493-kslzdy8q 28 18 2 2 CD cord-033493-kslzdy8q 28 19 ) ) -RRB- cord-033493-kslzdy8q 28 20 was be VBD cord-033493-kslzdy8q 28 21 used use VBN cord-033493-kslzdy8q 28 22 by by IN cord-033493-kslzdy8q 28 23 others other NNS cord-033493-kslzdy8q 28 24 as as IN cord-033493-kslzdy8q 28 25 a a DT cord-033493-kslzdy8q 28 26 starting starting NN cord-033493-kslzdy8q 28 27 material material NN cord-033493-kslzdy8q 28 28 for for IN cord-033493-kslzdy8q 28 29 the the DT cord-033493-kslzdy8q 28 30 synthesis synthesis NN cord-033493-kslzdy8q 28 31 of of IN cord-033493-kslzdy8q 28 32 pyrazolopyrimidines pyrazolopyrimidine NNS cord-033493-kslzdy8q 28 33 . . . cord-033493-kslzdy8q 29 1 22−27 22−27 NNP cord-033493-kslzdy8q 29 2 Studies Studies NNPS cord-033493-kslzdy8q 29 3 revealed reveal VBD cord-033493-kslzdy8q 29 4 that that IN cord-033493-kslzdy8q 29 5 5-aminopyrazoles 5-aminopyrazoles CD cord-033493-kslzdy8q 29 6 act act NN cord-033493-kslzdy8q 29 7 as as IN cord-033493-kslzdy8q 29 8 a a DT cord-033493-kslzdy8q 29 9 building building NN cord-033493-kslzdy8q 29 10 block block NN cord-033493-kslzdy8q 29 11 for for IN cord-033493-kslzdy8q 29 12 various various JJ cord-033493-kslzdy8q 29 13 functionalized functionalize VBN cord-033493-kslzdy8q 29 14 pyrazolopyrimidines pyrazolopyrimidine NNS cord-033493-kslzdy8q 29 15 as as IN cord-033493-kslzdy8q 29 16 purine purine NN cord-033493-kslzdy8q 29 17 analogs analog NNS cord-033493-kslzdy8q 29 18 . . . cord-033493-kslzdy8q 30 1 28−37 28−37 CD cord-033493-kslzdy8q 31 1 These these DT cord-033493-kslzdy8q 31 2 interesting interesting JJ cord-033493-kslzdy8q 31 3 results result NNS cord-033493-kslzdy8q 31 4 have have VBP cord-033493-kslzdy8q 31 5 promoted promote VBN cord-033493-kslzdy8q 31 6 our -PRON- PRP$ cord-033493-kslzdy8q 31 7 research research NN cord-033493-kslzdy8q 31 8 group group NN cord-033493-kslzdy8q 31 9 to to TO cord-033493-kslzdy8q 31 10 explore explore VB cord-033493-kslzdy8q 31 11 other other JJ cord-033493-kslzdy8q 31 12 synthetic synthetic JJ cord-033493-kslzdy8q 31 13 methods method NNS cord-033493-kslzdy8q 31 14 for for IN cord-033493-kslzdy8q 31 15 the the DT cord-033493-kslzdy8q 31 16 preparation preparation NN cord-033493-kslzdy8q 31 17 of of IN cord-033493-kslzdy8q 31 18 5-aminopyrazoles 5-aminopyrazoles CD cord-033493-kslzdy8q 31 19 for for IN cord-033493-kslzdy8q 31 20 synthesizing synthesize VBG cord-033493-kslzdy8q 31 21 pyrazolotriazines pyrazolotriazine NNS cord-033493-kslzdy8q 31 22 and and CC cord-033493-kslzdy8q 31 23 pyrazolopyrimidines pyrazolopyrimidine NNS cord-033493-kslzdy8q 31 24 and and CC cord-033493-kslzdy8q 31 25 investigating investigate VBG cord-033493-kslzdy8q 31 26 their -PRON- PRP$ cord-033493-kslzdy8q 31 27 use use NN cord-033493-kslzdy8q 31 28 as as IN cord-033493-kslzdy8q 31 29 antiviral antiviral JJ cord-033493-kslzdy8q 31 30 agents agent NNS cord-033493-kslzdy8q 31 31 in in IN cord-033493-kslzdy8q 31 32 chemotherapy chemotherapy NN cord-033493-kslzdy8q 31 33 . . . cord-033493-kslzdy8q 32 1 In in IN cord-033493-kslzdy8q 32 2 light light NN cord-033493-kslzdy8q 32 3 of of IN cord-033493-kslzdy8q 32 4 these these DT cord-033493-kslzdy8q 32 5 results result NNS cord-033493-kslzdy8q 32 6 and and CC cord-033493-kslzdy8q 32 7 as as IN cord-033493-kslzdy8q 32 8 part part NN cord-033493-kslzdy8q 32 9 of of IN cord-033493-kslzdy8q 32 10 our -PRON- PRP$ cord-033493-kslzdy8q 32 11 program program NN cord-033493-kslzdy8q 32 12 directed direct VBN cord-033493-kslzdy8q 32 13 toward toward IN cord-033493-kslzdy8q 32 14 the the DT cord-033493-kslzdy8q 32 15 preparation preparation NN cord-033493-kslzdy8q 32 16 of of IN cord-033493-kslzdy8q 32 17 potential potential JJ cord-033493-kslzdy8q 32 18 antiviral antiviral JJ cord-033493-kslzdy8q 32 19 antibiotics antibiotic NNS cord-033493-kslzdy8q 32 20 , , , cord-033493-kslzdy8q 32 21 the the DT cord-033493-kslzdy8q 32 22 present present JJ cord-033493-kslzdy8q 32 23 paper paper NN cord-033493-kslzdy8q 32 24 deals deal NNS cord-033493-kslzdy8q 32 25 with with IN cord-033493-kslzdy8q 32 26 a a DT cord-033493-kslzdy8q 32 27 novel novel JJ cord-033493-kslzdy8q 32 28 synthesis synthesis NN cord-033493-kslzdy8q 32 29 of of IN cord-033493-kslzdy8q 32 30 novel novel JJ cord-033493-kslzdy8q 32 31 benzamide benzamide NN cord-033493-kslzdy8q 32 32 - - HYPH cord-033493-kslzdy8q 32 33 based base VBN cord-033493-kslzdy8q 32 34 5-aminopyrazoles 5-aminopyrazoles CD cord-033493-kslzdy8q 32 35 and and CC cord-033493-kslzdy8q 32 36 their -PRON- PRP$ cord-033493-kslzdy8q 32 37 use use NN cord-033493-kslzdy8q 32 38 in in IN cord-033493-kslzdy8q 32 39 synthesizing synthesize VBG cord-033493-kslzdy8q 32 40 pyrazolo- pyrazolo- NN cord-033493-kslzdy8q 32 41 [ [ -LRB- cord-033493-kslzdy8q 32 42 5,1-c 5,1-c CD cord-033493-kslzdy8q 32 43 ] ] -RRB- cord-033493-kslzdy8q 32 44 triazine triazine NNP cord-033493-kslzdy8q 32 45 and and CC cord-033493-kslzdy8q 32 46 pyrazolo[1,5-a]pyrimidine pyrazolo[1,5-a]pyrimidine JJ cord-033493-kslzdy8q 32 47 ring ring NN cord-033493-kslzdy8q 32 48 systems system NNS cord-033493-kslzdy8q 32 49 using use VBG cord-033493-kslzdy8q 32 50 innovative innovative JJ cord-033493-kslzdy8q 32 51 synthetic synthetic JJ cord-033493-kslzdy8q 32 52 approaches approach NNS cord-033493-kslzdy8q 32 53 . . . cord-033493-kslzdy8q 33 1 Chemistry chemistry NN cord-033493-kslzdy8q 33 2 . . . cord-033493-kslzdy8q 34 1 It -PRON- PRP cord-033493-kslzdy8q 34 2 has have VBZ cord-033493-kslzdy8q 34 3 been be VBN cord-033493-kslzdy8q 34 4 found find VBN cord-033493-kslzdy8q 34 5 that that IN cord-033493-kslzdy8q 34 6 benzoyl benzoyl NN cord-033493-kslzdy8q 34 7 isothiocyanate isothiocyanate NN cord-033493-kslzdy8q 34 8 reacted react VBD cord-033493-kslzdy8q 34 9 with with IN cord-033493-kslzdy8q 34 10 malononitrile malononitrile NN cord-033493-kslzdy8q 34 11 in in IN cord-033493-kslzdy8q 34 12 potassium potassium NN cord-033493-kslzdy8q 34 13 hydroxide−ethanol hydroxide−ethanol NN cord-033493-kslzdy8q 34 14 with with IN cord-033493-kslzdy8q 34 15 heating heating NN cord-033493-kslzdy8q 34 16 to to TO cord-033493-kslzdy8q 34 17 give give VB cord-033493-kslzdy8q 34 18 the the DT cord-033493-kslzdy8q 34 19 corresponding correspond VBG cord-033493-kslzdy8q 34 20 stable stable JJ cord-033493-kslzdy8q 34 21 potassium potassium NN cord-033493-kslzdy8q 34 22 2cyano 2cyano CD cord-033493-kslzdy8q 34 23 - - : cord-033493-kslzdy8q 34 24 ethylene-1-thiolate ethylene-1-thiolate NN cord-033493-kslzdy8q 34 25 salt salt NN cord-033493-kslzdy8q 34 26 2 2 CD cord-033493-kslzdy8q 34 27 . . . cord-033493-kslzdy8q 35 1 5-Aminopyrazole 5-aminopyrazole CD cord-033493-kslzdy8q 35 2 4 4 CD cord-033493-kslzdy8q 35 3 was be VBD cord-033493-kslzdy8q 35 4 prepared prepare VBN cord-033493-kslzdy8q 35 5 by by IN cord-033493-kslzdy8q 35 6 alkylation alkylation NN cord-033493-kslzdy8q 35 7 of of IN cord-033493-kslzdy8q 35 8 the the DT cord-033493-kslzdy8q 35 9 potassium potassium NN cord-033493-kslzdy8q 35 10 2-cyano 2-cyano CD cord-033493-kslzdy8q 35 11 - - HYPH cord-033493-kslzdy8q 35 12 ethylene-1thiolate ethylene-1thiolate NN cord-033493-kslzdy8q 35 13 salt salt NN cord-033493-kslzdy8q 35 14 2 2 CD cord-033493-kslzdy8q 35 15 with with IN cord-033493-kslzdy8q 35 16 an an DT cord-033493-kslzdy8q 35 17 alkyl alkyl JJ cord-033493-kslzdy8q 35 18 halide halide NN cord-033493-kslzdy8q 35 19 at at IN cord-033493-kslzdy8q 35 20 room room NN cord-033493-kslzdy8q 35 21 temperature temperature NN cord-033493-kslzdy8q 35 22 to to TO cord-033493-kslzdy8q 35 23 offer offer VB cord-033493-kslzdy8q 35 24 N-(2,2-dicyano-1-(alkylthio)vinyl)benzamide N-(2,2-dicyano-1-(alkylthio)vinyl)benzamide NNP cord-033493-kslzdy8q 35 25 3 3 CD cord-033493-kslzdy8q 35 26 followed follow VBN cord-033493-kslzdy8q 35 27 by by IN cord-033493-kslzdy8q 35 28 a a DT cord-033493-kslzdy8q 35 29 reaction reaction NN cord-033493-kslzdy8q 35 30 with with IN cord-033493-kslzdy8q 35 31 hydrazine hydrazine NN cord-033493-kslzdy8q 35 32 hydrate hydrate NN cord-033493-kslzdy8q 35 33 by by IN cord-033493-kslzdy8q 35 34 refluxing refluxe VBG cord-033493-kslzdy8q 35 35 ethanol ethanol NN cord-033493-kslzdy8q 35 36 containing contain VBG cord-033493-kslzdy8q 35 37 a a DT cord-033493-kslzdy8q 35 38 catalytic catalytic JJ cord-033493-kslzdy8q 35 39 amount amount NN cord-033493-kslzdy8q 35 40 of of IN cord-033493-kslzdy8q 35 41 piperidine piperidine NN cord-033493-kslzdy8q 35 42 ( ( -LRB- cord-033493-kslzdy8q 35 43 Scheme scheme NN cord-033493-kslzdy8q 35 44 1 1 CD cord-033493-kslzdy8q 35 45 ) ) -RRB- cord-033493-kslzdy8q 35 46 . . . cord-033493-kslzdy8q 36 1 The the DT cord-033493-kslzdy8q 36 2 structures structure NNS cord-033493-kslzdy8q 36 3 of of IN cord-033493-kslzdy8q 36 4 3 3 CD cord-033493-kslzdy8q 36 5 and and CC cord-033493-kslzdy8q 36 6 4 4 CD cord-033493-kslzdy8q 36 7 were be VBD cord-033493-kslzdy8q 36 8 established establish VBN cord-033493-kslzdy8q 36 9 on on IN cord-033493-kslzdy8q 36 10 the the DT cord-033493-kslzdy8q 36 11 basis basis NN cord-033493-kslzdy8q 36 12 of of IN cord-033493-kslzdy8q 36 13 their -PRON- PRP$ cord-033493-kslzdy8q 36 14 elemental elemental JJ cord-033493-kslzdy8q 36 15 analysis analysis NN cord-033493-kslzdy8q 36 16 and and CC cord-033493-kslzdy8q 36 17 spectral spectral JJ cord-033493-kslzdy8q 36 18 data datum NNS cord-033493-kslzdy8q 36 19 ( ( -LRB- cord-033493-kslzdy8q 36 20 IR IR NNP cord-033493-kslzdy8q 36 21 , , , cord-033493-kslzdy8q 36 22 13 13 CD cord-033493-kslzdy8q 36 23 C c NN cord-033493-kslzdy8q 36 24 NMR NMR NNP cord-033493-kslzdy8q 36 25 , , , cord-033493-kslzdy8q 36 26 1 1 CD cord-033493-kslzdy8q 36 27 H h NN cord-033493-kslzdy8q 36 28 NMR nmr NN cord-033493-kslzdy8q 36 29 , , , cord-033493-kslzdy8q 36 30 and and CC cord-033493-kslzdy8q 36 31 MS MS NNP cord-033493-kslzdy8q 36 32 ) ) -RRB- cord-033493-kslzdy8q 36 33 . . . cord-033493-kslzdy8q 37 1 Structure structure NN cord-033493-kslzdy8q 37 2 4 4 CD cord-033493-kslzdy8q 37 3 was be VBD cord-033493-kslzdy8q 37 4 confirmed confirm VBN cord-033493-kslzdy8q 37 5 by by IN cord-033493-kslzdy8q 37 6 its -PRON- PRP$ cord-033493-kslzdy8q 37 7 mass mass NN cord-033493-kslzdy8q 37 8 ( ( -LRB- cord-033493-kslzdy8q 37 9 m m NNP cord-033493-kslzdy8q 37 10 / / SYM cord-033493-kslzdy8q 37 11 z z NNP cord-033493-kslzdy8q 37 12 227 227 CD cord-033493-kslzdy8q 37 13 ) ) -RRB- cord-033493-kslzdy8q 37 14 , , , cord-033493-kslzdy8q 37 15 which which WDT cord-033493-kslzdy8q 37 16 agrees agree VBZ cord-033493-kslzdy8q 37 17 with with IN cord-033493-kslzdy8q 37 18 its -PRON- PRP$ cord-033493-kslzdy8q 37 19 molecular molecular JJ cord-033493-kslzdy8q 37 20 formula formula NN cord-033493-kslzdy8q 37 21 C c NN cord-033493-kslzdy8q 37 22 11 11 CD cord-033493-kslzdy8q 37 23 H H NNP cord-033493-kslzdy8q 37 24 9 9 CD cord-033493-kslzdy8q 37 25 N n CD cord-033493-kslzdy8q 37 26 5 5 CD cord-033493-kslzdy8q 37 27 O. o. NN cord-033493-kslzdy8q 38 1 The the DT cord-033493-kslzdy8q 38 2 1 1 CD cord-033493-kslzdy8q 38 3 H h NN cord-033493-kslzdy8q 38 4 NMR nmr NN cord-033493-kslzdy8q 38 5 spectrum spectrum NN cord-033493-kslzdy8q 38 6 of of IN cord-033493-kslzdy8q 38 7 compound compound NN cord-033493-kslzdy8q 38 8 4 4 CD cord-033493-kslzdy8q 38 9 revealed reveal VBD cord-033493-kslzdy8q 38 10 a a DT cord-033493-kslzdy8q 38 11 broad broad JJ cord-033493-kslzdy8q 38 12 singlet singlet NN cord-033493-kslzdy8q 38 13 at at IN cord-033493-kslzdy8q 38 14 5.37 5.37 CD cord-033493-kslzdy8q 38 15 ppm ppm NN cord-033493-kslzdy8q 38 16 for for IN cord-033493-kslzdy8q 38 17 the the DT cord-033493-kslzdy8q 38 18 NH NH NNP cord-033493-kslzdy8q 38 19 2 2 CD cord-033493-kslzdy8q 38 20 group group NN cord-033493-kslzdy8q 38 21 , , , cord-033493-kslzdy8q 38 22 a a DT cord-033493-kslzdy8q 38 23 multiplet multiplet NN cord-033493-kslzdy8q 38 24 at at IN cord-033493-kslzdy8q 38 25 a a DT cord-033493-kslzdy8q 38 26 range range NN cord-033493-kslzdy8q 38 27 of of IN cord-033493-kslzdy8q 38 28 7.50−8.09 7.50−8.09 CD cord-033493-kslzdy8q 38 29 ppm ppm NN cord-033493-kslzdy8q 38 30 for for IN cord-033493-kslzdy8q 38 31 the the DT cord-033493-kslzdy8q 38 32 phenyl phenyl NNP cord-033493-kslzdy8q 38 33 moiety moiety NN cord-033493-kslzdy8q 38 34 , , , cord-033493-kslzdy8q 38 35 and and CC cord-033493-kslzdy8q 38 36 two two CD cord-033493-kslzdy8q 38 37 broad broad JJ cord-033493-kslzdy8q 38 38 singlets singlet NNS cord-033493-kslzdy8q 38 39 at at IN cord-033493-kslzdy8q 38 40 11.73 11.73 CD cord-033493-kslzdy8q 38 41 and and CC cord-033493-kslzdy8q 38 42 12.33 12.33 CD cord-033493-kslzdy8q 38 43 ppm ppm NN cord-033493-kslzdy8q 38 44 assigned assign VBN cord-033493-kslzdy8q 38 45 to to IN cord-033493-kslzdy8q 38 46 two two CD cord-033493-kslzdy8q 38 47 NH NH NNP cord-033493-kslzdy8q 38 48 groups group NNS cord-033493-kslzdy8q 38 49 . . . cord-033493-kslzdy8q 39 1 The the DT cord-033493-kslzdy8q 39 2 reactivity reactivity NN cord-033493-kslzdy8q 39 3 of of IN cord-033493-kslzdy8q 39 4 5-aminopyrazole 5-aminopyrazole CD cord-033493-kslzdy8q 39 5 derivative derivative JJ cord-033493-kslzdy8q 39 6 4 4 CD cord-033493-kslzdy8q 39 7 to to TO cord-033493-kslzdy8q 39 8 form form VB cord-033493-kslzdy8q 39 9 the the DT cord-033493-kslzdy8q 39 10 diazonium diazonium NN cord-033493-kslzdy8q 39 11 salt salt NN cord-033493-kslzdy8q 39 12 5 5 CD cord-033493-kslzdy8q 39 13 was be VBD cord-033493-kslzdy8q 39 14 studied study VBN cord-033493-kslzdy8q 39 15 , , , cord-033493-kslzdy8q 39 16 and and CC cord-033493-kslzdy8q 39 17 the the DT cord-033493-kslzdy8q 39 18 latter latter JJ cord-033493-kslzdy8q 39 19 was be VBD cord-033493-kslzdy8q 39 20 coupled couple VBN cord-033493-kslzdy8q 39 21 with with IN cord-033493-kslzdy8q 39 22 malononitrile malononitrile NN cord-033493-kslzdy8q 39 23 or or CC cord-033493-kslzdy8q 39 24 ethyl ethyl NN cord-033493-kslzdy8q 39 25 cyanoacetate cyanoacetate NN cord-033493-kslzdy8q 39 26 in in IN cord-033493-kslzdy8q 39 27 sodium sodium NN cord-033493-kslzdy8q 39 28 acetate acetate NN cord-033493-kslzdy8q 39 29 / / SYM cord-033493-kslzdy8q 39 30 EtOH EtOH NNP cord-033493-kslzdy8q 39 31 to to TO cord-033493-kslzdy8q 39 32 give give VB cord-033493-kslzdy8q 39 33 the the DT cord-033493-kslzdy8q 39 34 corresponding correspond VBG cord-033493-kslzdy8q 39 35 pyrazolotriazines pyrazolotriazine NNS cord-033493-kslzdy8q 39 36 6a 6a NNP cord-033493-kslzdy8q 39 37 , , , cord-033493-kslzdy8q 39 38 b b LS cord-033493-kslzdy8q 39 39 ( ( -LRB- cord-033493-kslzdy8q 39 40 Scheme scheme NN cord-033493-kslzdy8q 39 41 2 2 CD cord-033493-kslzdy8q 39 42 ) ) -RRB- cord-033493-kslzdy8q 39 43 . . . cord-033493-kslzdy8q 40 1 The the DT cord-033493-kslzdy8q 40 2 structures structure NNS cord-033493-kslzdy8q 40 3 of of IN cord-033493-kslzdy8q 40 4 the the DT cord-033493-kslzdy8q 40 5 resultant resultant JJ cord-033493-kslzdy8q 40 6 N-(pyrazolo N-(pyrazolo NNP cord-033493-kslzdy8q 40 7 [ [ -LRB- cord-033493-kslzdy8q 40 8 5,1-c 5,1-c CD cord-033493-kslzdy8q 40 9 ] ] -RRB- cord-033493-kslzdy8q 40 10 [ [ -LRB- cord-033493-kslzdy8q 40 11 1 1 CD cord-033493-kslzdy8q 40 12 , , , cord-033493-kslzdy8q 40 13 2 2 CD cord-033493-kslzdy8q 40 14 , , , cord-033493-kslzdy8q 40 15 4 4 CD cord-033493-kslzdy8q 40 16 ] ] -RRB- cord-033493-kslzdy8q 40 17 triazin-7-yl)benzamides triazin-7-yl)benzamides NNP cord-033493-kslzdy8q 40 18 6a 6a CD cord-033493-kslzdy8q 40 19 , , , cord-033493-kslzdy8q 40 20 b b NNP cord-033493-kslzdy8q 40 21 were be VBD cord-033493-kslzdy8q 40 22 confirmed confirm VBN cord-033493-kslzdy8q 40 23 according accord VBG cord-033493-kslzdy8q 40 24 to to IN cord-033493-kslzdy8q 40 25 their -PRON- PRP$ cord-033493-kslzdy8q 40 26 spectral spectral JJ cord-033493-kslzdy8q 40 27 data datum NNS cord-033493-kslzdy8q 40 28 . . . cord-033493-kslzdy8q 41 1 Thus thus RB cord-033493-kslzdy8q 41 2 , , , cord-033493-kslzdy8q 41 3 the the DT cord-033493-kslzdy8q 41 4 1 1 CD cord-033493-kslzdy8q 41 5 H h NN cord-033493-kslzdy8q 41 6 NMR nmr NN cord-033493-kslzdy8q 41 7 spectrum spectrum NN cord-033493-kslzdy8q 41 8 for for IN cord-033493-kslzdy8q 41 9 compound compound NN cord-033493-kslzdy8q 41 10 6a 6a NNP cord-033493-kslzdy8q 41 11 revealed reveal VBD cord-033493-kslzdy8q 41 12 a a DT cord-033493-kslzdy8q 41 13 multiplet multiplet NN cord-033493-kslzdy8q 41 14 at at IN cord-033493-kslzdy8q 41 15 a a DT cord-033493-kslzdy8q 41 16 range range NN cord-033493-kslzdy8q 41 17 of of IN cord-033493-kslzdy8q 41 18 7.46−8.19 7.46−8.19 CD cord-033493-kslzdy8q 41 19 ppm ppm NN cord-033493-kslzdy8q 41 20 for for IN cord-033493-kslzdy8q 41 21 the the DT cord-033493-kslzdy8q 41 22 presence presence NN cord-033493-kslzdy8q 41 23 of of IN cord-033493-kslzdy8q 41 24 the the DT cord-033493-kslzdy8q 41 25 phenyl phenyl NNP cord-033493-kslzdy8q 41 26 group group NN cord-033493-kslzdy8q 41 27 , , , cord-033493-kslzdy8q 41 28 a a DT cord-033493-kslzdy8q 41 29 broad broad JJ cord-033493-kslzdy8q 41 30 singlet singlet NN cord-033493-kslzdy8q 41 31 at at IN cord-033493-kslzdy8q 41 32 3.60 3.60 CD cord-033493-kslzdy8q 41 33 ppm ppm NN cord-033493-kslzdy8q 41 34 for for IN cord-033493-kslzdy8q 41 35 the the DT cord-033493-kslzdy8q 41 36 NH NH NNP cord-033493-kslzdy8q 41 37 2 2 CD cord-033493-kslzdy8q 41 38 group group NN cord-033493-kslzdy8q 41 39 , , , cord-033493-kslzdy8q 41 40 and and CC cord-033493-kslzdy8q 41 41 a a DT cord-033493-kslzdy8q 41 42 broad broad JJ cord-033493-kslzdy8q 41 43 singlet singlet NN cord-033493-kslzdy8q 41 44 at at IN cord-033493-kslzdy8q 41 45 10.47 10.47 CD cord-033493-kslzdy8q 41 46 ppm ppm NN cord-033493-kslzdy8q 41 47 for for IN cord-033493-kslzdy8q 41 48 an an DT cord-033493-kslzdy8q 41 49 NH NH NNP cord-033493-kslzdy8q 41 50 group group NN cord-033493-kslzdy8q 41 51 . . . cord-033493-kslzdy8q 42 1 It -PRON- PRP cord-033493-kslzdy8q 42 2 was be VBD cord-033493-kslzdy8q 42 3 found find VBN cord-033493-kslzdy8q 42 4 that that IN cord-033493-kslzdy8q 42 5 the the DT cord-033493-kslzdy8q 42 6 5-aminopyrazole 5-aminopyrazole CD cord-033493-kslzdy8q 42 7 4 4 CD cord-033493-kslzdy8q 42 8 reacts react VBZ cord-033493-kslzdy8q 42 9 with with IN cord-033493-kslzdy8q 42 10 the the DT cord-033493-kslzdy8q 42 11 sodium sodium NN cord-033493-kslzdy8q 42 12 salts salt NNS cord-033493-kslzdy8q 42 13 of of IN cord-033493-kslzdy8q 42 14 ( ( -LRB- cord-033493-kslzdy8q 42 15 hydroxymethylene)cycloalkanones hydroxymethylene)cycloalkanones NNP cord-033493-kslzdy8q 42 16 7a 7a NN cord-033493-kslzdy8q 42 17 , , , cord-033493-kslzdy8q 42 18 b b LS cord-033493-kslzdy8q 42 19 in in IN cord-033493-kslzdy8q 42 20 the the DT cord-033493-kslzdy8q 42 21 presence presence NN cord-033493-kslzdy8q 42 22 of of IN cord-033493-kslzdy8q 42 23 piperidine piperidine NN cord-033493-kslzdy8q 42 24 acetate−acetic acetate−acetic CD cord-033493-kslzdy8q 42 25 acid acid NN cord-033493-kslzdy8q 42 26 to to TO cord-033493-kslzdy8q 42 27 give give VB cord-033493-kslzdy8q 42 28 an an DT cord-033493-kslzdy8q 42 29 adduct adduct NN cord-033493-kslzdy8q 42 30 , , , cord-033493-kslzdy8q 42 31 where where WRB cord-033493-kslzdy8q 42 32 the the DT cord-033493-kslzdy8q 42 33 structure structure NN cord-033493-kslzdy8q 42 34 of of IN cord-033493-kslzdy8q 42 35 8a 8a NN cord-033493-kslzdy8q 42 36 , , , cord-033493-kslzdy8q 42 37 b b NNP cord-033493-kslzdy8q 42 38 was be VBD cord-033493-kslzdy8q 42 39 established establish VBN cord-033493-kslzdy8q 42 40 . . . cord-033493-kslzdy8q 43 1 The the DT cord-033493-kslzdy8q 43 2 reaction reaction NN cord-033493-kslzdy8q 43 3 begins begin VBZ cord-033493-kslzdy8q 43 4 with with IN cord-033493-kslzdy8q 43 5 an an DT cord-033493-kslzdy8q 43 6 initial initial JJ cord-033493-kslzdy8q 43 7 nucleophilic nucleophilic JJ cord-033493-kslzdy8q 43 8 attack attack NN cord-033493-kslzdy8q 43 9 from from IN cord-033493-kslzdy8q 43 10 the the DT cord-033493-kslzdy8q 43 11 external external JJ cord-033493-kslzdy8q 43 12 amino amino NN cord-033493-kslzdy8q 43 13 group group NN cord-033493-kslzdy8q 43 14 to to IN cord-033493-kslzdy8q 43 15 the the DT cord-033493-kslzdy8q 43 16 formyl formyl NNP cord-033493-kslzdy8q 43 17 group group NN cord-033493-kslzdy8q 43 18 followed follow VBN cord-033493-kslzdy8q 43 19 by by IN cord-033493-kslzdy8q 43 20 cyclization cyclization NN cord-033493-kslzdy8q 43 21 and and CC cord-033493-kslzdy8q 43 22 then then RB cord-033493-kslzdy8q 43 23 removal removal NN cord-033493-kslzdy8q 43 24 of of IN cord-033493-kslzdy8q 43 25 one one CD cord-033493-kslzdy8q 43 26 molecule molecule NN cord-033493-kslzdy8q 43 27 of of IN cord-033493-kslzdy8q 43 28 water water NN cord-033493-kslzdy8q 43 29 to to TO cord-033493-kslzdy8q 43 30 produce produce VB cord-033493-kslzdy8q 43 31 the the DT cord-033493-kslzdy8q 43 32 angular angular JJ cord-033493-kslzdy8q 43 33 tricyclic tricyclic NN cord-033493-kslzdy8q 43 34 compounds compound NNS cord-033493-kslzdy8q 43 35 8a 8a NNP cord-033493-kslzdy8q 43 36 , , , cord-033493-kslzdy8q 43 37 b b NNP cord-033493-kslzdy8q 43 38 . . . cord-033493-kslzdy8q 44 1 In in IN cord-033493-kslzdy8q 44 2 the the DT cord-033493-kslzdy8q 44 3 presence presence NN cord-033493-kslzdy8q 44 4 of of IN cord-033493-kslzdy8q 44 5 an an DT cord-033493-kslzdy8q 44 6 acid acid NN cord-033493-kslzdy8q 44 7 medium medium NN cord-033493-kslzdy8q 44 8 , , , cord-033493-kslzdy8q 44 9 first first RB cord-033493-kslzdy8q 44 10 , , , cord-033493-kslzdy8q 44 11 the the DT cord-033493-kslzdy8q 44 12 protonation protonation NN cord-033493-kslzdy8q 44 13 of of IN cord-033493-kslzdy8q 44 14 the the DT cord-033493-kslzdy8q 44 15 ring ring NN cord-033493-kslzdy8q 44 16 nitrogen nitrogen NN cord-033493-kslzdy8q 44 17 occurs occur VBZ cord-033493-kslzdy8q 44 18 , , , cord-033493-kslzdy8q 44 19 which which WDT cord-033493-kslzdy8q 44 20 is be VBZ cord-033493-kslzdy8q 44 21 the the DT cord-033493-kslzdy8q 44 22 most most RBS cord-033493-kslzdy8q 44 23 nucleophilic nucleophilic JJ cord-033493-kslzdy8q 44 24 center center NN cord-033493-kslzdy8q 44 25 38−43 38−43 CD cord-033493-kslzdy8q 44 26 in in IN cord-033493-kslzdy8q 44 27 compound compound NN cord-033493-kslzdy8q 44 28 4 4 CD cord-033493-kslzdy8q 44 29 , , , cord-033493-kslzdy8q 44 30 which which WDT cord-033493-kslzdy8q 44 31 directs direct VBZ cord-033493-kslzdy8q 44 32 the the DT cord-033493-kslzdy8q 44 33 exocyclic exocyclic NNP cord-033493-kslzdy8q 44 34 amino amino NNP cord-033493-kslzdy8q 44 35 group group NN cord-033493-kslzdy8q 44 36 to to TO cord-033493-kslzdy8q 44 37 attack attack VB cord-033493-kslzdy8q 44 38 the the DT cord-033493-kslzdy8q 44 39 unhindered unhindered JJ cord-033493-kslzdy8q 44 40 formyl formyl NNP cord-033493-kslzdy8q 44 41 group group NNP cord-033493-kslzdy8q 44 42 of of IN cord-033493-kslzdy8q 44 43 7 7 CD cord-033493-kslzdy8q 44 44 to to TO cord-033493-kslzdy8q 44 45 yield yield VB cord-033493-kslzdy8q 44 46 compounds compound NNS cord-033493-kslzdy8q 44 47 8a 8a NN cord-033493-kslzdy8q 44 48 , , , cord-033493-kslzdy8q 44 49 b b LS cord-033493-kslzdy8q 44 50 ( ( -LRB- cord-033493-kslzdy8q 44 51 Scheme scheme NN cord-033493-kslzdy8q 44 52 3 3 CD cord-033493-kslzdy8q 44 53 ) ) -RRB- cord-033493-kslzdy8q 44 54 . . . cord-033493-kslzdy8q 45 1 The the DT cord-033493-kslzdy8q 45 2 1 1 CD cord-033493-kslzdy8q 45 3 H h NN cord-033493-kslzdy8q 45 4 NMR nmr NN cord-033493-kslzdy8q 45 5 spectrum spectrum NN cord-033493-kslzdy8q 45 6 of of IN cord-033493-kslzdy8q 45 7 8a 8a NNP cord-033493-kslzdy8q 45 8 showed show VBD cord-033493-kslzdy8q 45 9 the the DT cord-033493-kslzdy8q 45 10 existence existence NN cord-033493-kslzdy8q 45 11 of of IN cord-033493-kslzdy8q 45 12 a a DT cord-033493-kslzdy8q 45 13 signal signal NN cord-033493-kslzdy8q 45 14 at at IN cord-033493-kslzdy8q 45 15 δ δ NN cord-033493-kslzdy8q 45 16 8.80 8.80 CD cord-033493-kslzdy8q 45 17 ppm ppm NN cord-033493-kslzdy8q 45 18 assigned assign VBN cord-033493-kslzdy8q 45 19 to to IN cord-033493-kslzdy8q 45 20 a a DT cord-033493-kslzdy8q 45 21 pyrimidine pyrimidine NN cord-033493-kslzdy8q 45 22 - - HYPH cord-033493-kslzdy8q 45 23 H h NN cord-033493-kslzdy8q 45 24 proton proton NN cord-033493-kslzdy8q 45 25 . . . cord-033493-kslzdy8q 46 1 The the DT cord-033493-kslzdy8q 46 2 5-aminopyrazole 5-aminopyrazole CD cord-033493-kslzdy8q 46 3 4 4 CD cord-033493-kslzdy8q 46 4 reacted react VBD cord-033493-kslzdy8q 46 5 with with IN cord-033493-kslzdy8q 46 6 arylmethylene arylmethylene JJ cord-033493-kslzdy8q 46 7 malononitriles malononitrile NNS cord-033493-kslzdy8q 46 8 9 9 CD cord-033493-kslzdy8q 46 9 with with IN cord-033493-kslzdy8q 46 10 piperidine piperidine NN cord-033493-kslzdy8q 46 11 as as IN cord-033493-kslzdy8q 46 12 a a DT cord-033493-kslzdy8q 46 13 catalyst catalyst NN cord-033493-kslzdy8q 46 14 to to TO cord-033493-kslzdy8q 46 15 give give VB cord-033493-kslzdy8q 46 16 the the DT cord-033493-kslzdy8q 46 17 pyrazolo[1,5-a]pyrimidines pyrazolo[1,5-a]pyrimidines NNPS cord-033493-kslzdy8q 46 18 10a−c 10a−c CD cord-033493-kslzdy8q 46 19 . . . cord-033493-kslzdy8q 47 1 The the DT cord-033493-kslzdy8q 47 2 reaction reaction NN cord-033493-kslzdy8q 47 3 proceeded proceed VBD cord-033493-kslzdy8q 47 4 by by IN cord-033493-kslzdy8q 47 5 Michael Michael NNP cord-033493-kslzdy8q 47 6 addition addition NN cord-033493-kslzdy8q 47 7 of of IN cord-033493-kslzdy8q 47 8 the the DT cord-033493-kslzdy8q 47 9 exocyclic exocyclic NNP cord-033493-kslzdy8q 47 10 amino amino NNP cord-033493-kslzdy8q 47 11 group group NN cord-033493-kslzdy8q 47 12 of of IN cord-033493-kslzdy8q 47 13 4 4 CD cord-033493-kslzdy8q 47 14 to to IN cord-033493-kslzdy8q 47 15 the the DT cord-033493-kslzdy8q 47 16 double double JJ cord-033493-kslzdy8q 47 17 bond bond NN cord-033493-kslzdy8q 47 18 of of IN cord-033493-kslzdy8q 47 19 9 9 CD cord-033493-kslzdy8q 47 20 followed follow VBN cord-033493-kslzdy8q 47 21 by by IN cord-033493-kslzdy8q 47 22 cyclization cyclization NN cord-033493-kslzdy8q 47 23 through through IN cord-033493-kslzdy8q 47 24 the the DT cord-033493-kslzdy8q 47 25 addition addition NN cord-033493-kslzdy8q 47 26 of of IN cord-033493-kslzdy8q 47 27 the the DT cord-033493-kslzdy8q 47 28 ring ring NN cord-033493-kslzdy8q 47 29 NH NH NNP cord-033493-kslzdy8q 47 30 to to IN cord-033493-kslzdy8q 47 31 the the DT cord-033493-kslzdy8q 47 32 cyano cyano NNP cord-033493-kslzdy8q 47 33 group group NN cord-033493-kslzdy8q 47 34 to to TO cord-033493-kslzdy8q 47 35 give give VB cord-033493-kslzdy8q 47 36 the the DT cord-033493-kslzdy8q 47 37 pyrazolo[1,5a]pyrimidines pyrazolo[1,5a]pyrimidine NNS cord-033493-kslzdy8q 47 38 10 10 CD cord-033493-kslzdy8q 47 39 ( ( -LRB- cord-033493-kslzdy8q 47 40 Scheme scheme NN cord-033493-kslzdy8q 47 41 3 3 CD cord-033493-kslzdy8q 47 42 ) ) -RRB- cord-033493-kslzdy8q 47 43 . . . cord-033493-kslzdy8q 48 1 The the DT cord-033493-kslzdy8q 48 2 structures structure NNS cord-033493-kslzdy8q 48 3 of of IN cord-033493-kslzdy8q 48 4 10a−c 10a−c NNS cord-033493-kslzdy8q 48 5 were be VBD cord-033493-kslzdy8q 48 6 confirmed confirm VBN cord-033493-kslzdy8q 48 7 by by IN cord-033493-kslzdy8q 48 8 1 1 CD cord-033493-kslzdy8q 48 9 H h NN cord-033493-kslzdy8q 48 10 NMR nmr NN cord-033493-kslzdy8q 48 11 , , , cord-033493-kslzdy8q 48 12 which which WDT cord-033493-kslzdy8q 48 13 revealed reveal VBD cord-033493-kslzdy8q 48 14 for for IN cord-033493-kslzdy8q 48 15 compound compound NN cord-033493-kslzdy8q 48 16 10b 10b NNS cord-033493-kslzdy8q 48 17 a a DT cord-033493-kslzdy8q 48 18 singlet singlet NN cord-033493-kslzdy8q 48 19 at at IN cord-033493-kslzdy8q 48 20 3.88 3.88 CD cord-033493-kslzdy8q 48 21 ppm ppm NN cord-033493-kslzdy8q 48 22 assigned assign VBN cord-033493-kslzdy8q 48 23 to to IN cord-033493-kslzdy8q 48 24 the the DT cord-033493-kslzdy8q 48 25 OCH OCH NNP cord-033493-kslzdy8q 48 26 3 3 CD cord-033493-kslzdy8q 48 27 group group NN cord-033493-kslzdy8q 48 28 , , , cord-033493-kslzdy8q 48 29 a a DT cord-033493-kslzdy8q 48 30 singlet singlet NN cord-033493-kslzdy8q 48 31 at at IN cord-033493-kslzdy8q 48 32 9.18 9.18 CD cord-033493-kslzdy8q 48 33 ppm ppm NN cord-033493-kslzdy8q 48 34 assigned assign VBN cord-033493-kslzdy8q 48 35 to to IN cord-033493-kslzdy8q 48 36 the the DT cord-033493-kslzdy8q 48 37 NH NH NNP cord-033493-kslzdy8q 48 38 2 2 CD cord-033493-kslzdy8q 48 39 group group NN cord-033493-kslzdy8q 48 40 , , , cord-033493-kslzdy8q 48 41 a a DT cord-033493-kslzdy8q 48 42 multiplet multiplet NN cord-033493-kslzdy8q 48 43 at at IN cord-033493-kslzdy8q 48 44 a a DT cord-033493-kslzdy8q 48 45 range range NN cord-033493-kslzdy8q 48 46 of of IN cord-033493-kslzdy8q 48 47 7.15−8.23 7.15−8.23 CD cord-033493-kslzdy8q 48 48 ppm ppm NN cord-033493-kslzdy8q 48 49 for for IN cord-033493-kslzdy8q 48 50 aromatic aromatic JJ cord-033493-kslzdy8q 48 51 protons proton NNS cord-033493-kslzdy8q 48 52 , , , cord-033493-kslzdy8q 48 53 and and CC cord-033493-kslzdy8q 48 54 a a DT cord-033493-kslzdy8q 48 55 broad broad JJ cord-033493-kslzdy8q 48 56 singlet singlet NN cord-033493-kslzdy8q 48 57 at at IN cord-033493-kslzdy8q 48 58 12.19 12.19 CD cord-033493-kslzdy8q 48 59 ppm ppm NN cord-033493-kslzdy8q 48 60 to to TO cord-033493-kslzdy8q 48 61 indicate indicate VB cord-033493-kslzdy8q 48 62 the the DT cord-033493-kslzdy8q 48 63 presence presence NN cord-033493-kslzdy8q 48 64 of of IN cord-033493-kslzdy8q 48 65 the the DT cord-033493-kslzdy8q 48 66 NH NH NNP cord-033493-kslzdy8q 48 67 group group NN cord-033493-kslzdy8q 48 68 . . . cord-033493-kslzdy8q 49 1 The the DT cord-033493-kslzdy8q 49 2 reactivity reactivity NN cord-033493-kslzdy8q 49 3 of of IN cord-033493-kslzdy8q 49 4 diketones diketone NNS cord-033493-kslzdy8q 49 5 and and CC cord-033493-kslzdy8q 49 6 keto keto NNP cord-033493-kslzdy8q 49 7 esters ester NNS cord-033493-kslzdy8q 49 8 such such JJ cord-033493-kslzdy8q 49 9 as as IN cord-033493-kslzdy8q 49 10 acetyl acetyl NN cord-033493-kslzdy8q 49 11 acetone acetone NN cord-033493-kslzdy8q 49 12 11a 11a NNS cord-033493-kslzdy8q 49 13 and and CC cord-033493-kslzdy8q 49 14 ethyl ethyl NN cord-033493-kslzdy8q 49 15 acetoacetate acetoacetate NN cord-033493-kslzdy8q 49 16 11b 11b NNS cord-033493-kslzdy8q 50 1 with with IN cord-033493-kslzdy8q 50 2 5-aminopyrazole 5-aminopyrazole CD cord-033493-kslzdy8q 50 3 4 4 CD cord-033493-kslzdy8q 50 4 was be VBD cord-033493-kslzdy8q 50 5 studied study VBN cord-033493-kslzdy8q 50 6 through through IN cord-033493-kslzdy8q 50 7 a a DT cord-033493-kslzdy8q 50 8 reaction reaction NN cord-033493-kslzdy8q 50 9 with with IN cord-033493-kslzdy8q 50 10 piperidine piperidine NN cord-033493-kslzdy8q 50 11 and and CC cord-033493-kslzdy8q 50 12 boiling boil VBG cord-033493-kslzdy8q 50 13 ethanol ethanol NN cord-033493-kslzdy8q 50 14 to to TO cord-033493-kslzdy8q 50 15 afford afford VB cord-033493-kslzdy8q 50 16 the the DT cord-033493-kslzdy8q 50 17 corresponding correspond VBG cord-033493-kslzdy8q 50 18 pyrazolo[1,5-a]pyrimidines pyrazolo[1,5-a]pyrimidines NNPS cord-033493-kslzdy8q 50 19 12a 12a NNS cord-033493-kslzdy8q 50 20 , , , cord-033493-kslzdy8q 50 21 b b NN cord-033493-kslzdy8q 50 22 . . . cord-033493-kslzdy8q 51 1 An an DT cord-033493-kslzdy8q 51 2 attempt attempt NN cord-033493-kslzdy8q 51 3 to to TO cord-033493-kslzdy8q 51 4 react react VB cord-033493-kslzdy8q 51 5 benzoyl benzoyl NN cord-033493-kslzdy8q 51 6 isothiocyanate isothiocyanate NN cord-033493-kslzdy8q 51 7 with with IN cord-033493-kslzdy8q 51 8 ethyl ethyl NN cord-033493-kslzdy8q 51 9 cyanoacetate cyanoacetate NN cord-033493-kslzdy8q 51 10 in in IN cord-033493-kslzdy8q 51 11 KOH−EtOH KOH−EtOH NNP cord-033493-kslzdy8q 51 12 with with IN cord-033493-kslzdy8q 51 13 heating heating NN cord-033493-kslzdy8q 51 14 followed follow VBN cord-033493-kslzdy8q 51 15 by by IN cord-033493-kslzdy8q 51 16 alkylation alkylation NN cord-033493-kslzdy8q 51 17 with with IN cord-033493-kslzdy8q 51 18 methyl methyl NN cord-033493-kslzdy8q 51 19 iodides iodide NNS cord-033493-kslzdy8q 51 20 at at IN cord-033493-kslzdy8q 51 21 room room NN cord-033493-kslzdy8q 51 22 temperature temperature NN cord-033493-kslzdy8q 51 23 has have VBZ cord-033493-kslzdy8q 51 24 resulted result VBN cord-033493-kslzdy8q 51 25 in in IN cord-033493-kslzdy8q 51 26 the the DT cord-033493-kslzdy8q 51 27 formation formation NN cord-033493-kslzdy8q 51 28 of of IN cord-033493-kslzdy8q 51 29 the the DT cord-033493-kslzdy8q 51 30 corresponding correspond VBG cord-033493-kslzdy8q 51 31 ( ( -LRB- cord-033493-kslzdy8q 51 32 E)-ethyl E)-ethyl NNP cord-033493-kslzdy8q 51 33 3benzamido-2-cyano-3-(methylthio)acrylate 3benzamido-2-cyano-3-(methylthio)acrylate CD cord-033493-kslzdy8q 51 34 14 14 CD cord-033493-kslzdy8q 51 35 . . . cord-033493-kslzdy8q 52 1 The the DT cord-033493-kslzdy8q 52 2 reaction reaction NN cord-033493-kslzdy8q 52 3 of of IN cord-033493-kslzdy8q 52 4 ( ( -LRB- cord-033493-kslzdy8q 52 5 E)-ethyl E)-ethyl NNP cord-033493-kslzdy8q 52 6 3-benzamido-2-cyano-3-(methylthio)acrylate 3-benzamido-2-cyano-3-(methylthio)acrylate CD cord-033493-kslzdy8q 52 7 14 14 CD cord-033493-kslzdy8q 52 8 with with IN cord-033493-kslzdy8q 52 9 hydrazine hydrazine NN cord-033493-kslzdy8q 52 10 was be VBD cord-033493-kslzdy8q 52 11 investigated investigate VBN cord-033493-kslzdy8q 52 12 . . . cord-033493-kslzdy8q 53 1 The the DT cord-033493-kslzdy8q 53 2 reaction reaction NN cord-033493-kslzdy8q 53 3 between between IN cord-033493-kslzdy8q 53 4 14 14 CD cord-033493-kslzdy8q 53 5 and and CC cord-033493-kslzdy8q 53 6 hydrazine hydrazine NN cord-033493-kslzdy8q 53 7 gave give VBD cord-033493-kslzdy8q 53 8 a a DT cord-033493-kslzdy8q 53 9 product product NN cord-033493-kslzdy8q 53 10 whose whose WP$ cord-033493-kslzdy8q 53 11 mass mass NN cord-033493-kslzdy8q 53 12 spectra spectrum NNS cord-033493-kslzdy8q 53 13 were be VBD cord-033493-kslzdy8q 53 14 not not RB cord-033493-kslzdy8q 53 15 consistent consistent JJ cord-033493-kslzdy8q 53 16 with with IN cord-033493-kslzdy8q 53 17 the the DT cord-033493-kslzdy8q 53 18 proposed propose VBN cord-033493-kslzdy8q 53 19 pyrazole pyrazole NN cord-033493-kslzdy8q 53 20 structure structure NN cord-033493-kslzdy8q 53 21 16 16 CD cord-033493-kslzdy8q 53 22 , , , cord-033493-kslzdy8q 53 23 and and CC cord-033493-kslzdy8q 53 24 other other JJ cord-033493-kslzdy8q 53 25 spectroscopic spectroscopic JJ cord-033493-kslzdy8q 53 26 measurements measurement NNS cord-033493-kslzdy8q 53 27 did do VBD cord-033493-kslzdy8q 53 28 not not RB cord-033493-kslzdy8q 53 29 allow allow VB cord-033493-kslzdy8q 53 30 us -PRON- PRP cord-033493-kslzdy8q 53 31 to to TO cord-033493-kslzdy8q 53 32 unambiguously unambiguously RB cord-033493-kslzdy8q 53 33 identify identify VB cord-033493-kslzdy8q 53 34 the the DT cord-033493-kslzdy8q 53 35 product product NN cord-033493-kslzdy8q 53 36 , , , cord-033493-kslzdy8q 53 37 and and CC cord-033493-kslzdy8q 53 38 thus thus RB cord-033493-kslzdy8q 53 39 , , , cord-033493-kslzdy8q 53 40 the the DT cord-033493-kslzdy8q 53 41 X x NN cord-033493-kslzdy8q 53 42 - - NN cord-033493-kslzdy8q 53 43 ray ray NNP cord-033493-kslzdy8q 53 44 crystal crystal NN cord-033493-kslzdy8q 53 45 structure structure NN cord-033493-kslzdy8q 53 46 was be VBD cord-033493-kslzdy8q 53 47 determined determine VBN cord-033493-kslzdy8q 53 48 as as IN cord-033493-kslzdy8q 53 49 shown show VBN cord-033493-kslzdy8q 53 50 in in IN cord-033493-kslzdy8q 53 51 Figure Figure NNP cord-033493-kslzdy8q 53 52 3 3 CD cord-033493-kslzdy8q 53 53 , , , cord-033493-kslzdy8q 53 54 44 44 CD cord-033493-kslzdy8q 53 55 confirming confirm VBG cord-033493-kslzdy8q 53 56 the the DT cord-033493-kslzdy8q 53 57 exclusive exclusive JJ cord-033493-kslzdy8q 53 58 presence presence NN cord-033493-kslzdy8q 53 59 of of IN cord-033493-kslzdy8q 53 60 the the DT cord-033493-kslzdy8q 53 61 triazole triazole NNP cord-033493-kslzdy8q 53 62 derivative derivative NNP cord-033493-kslzdy8q 53 63 19 19 CD cord-033493-kslzdy8q 53 64 as as IN cord-033493-kslzdy8q 53 65 the the DT cord-033493-kslzdy8q 53 66 sole sole JJ cord-033493-kslzdy8q 53 67 product product NN cord-033493-kslzdy8q 53 68 in in IN cord-033493-kslzdy8q 53 69 the the DT cord-033493-kslzdy8q 53 70 solid solid JJ cord-033493-kslzdy8q 53 71 state state NN cord-033493-kslzdy8q 53 72 . . . cord-033493-kslzdy8q 54 1 The the DT cord-033493-kslzdy8q 54 2 formation formation NN cord-033493-kslzdy8q 54 3 of of IN cord-033493-kslzdy8q 54 4 19 19 CD cord-033493-kslzdy8q 54 5 from from IN cord-033493-kslzdy8q 54 6 the the DT cord-033493-kslzdy8q 54 7 reaction reaction NN cord-033493-kslzdy8q 54 8 of of IN cord-033493-kslzdy8q 54 9 14 14 CD cord-033493-kslzdy8q 54 10 and and CC cord-033493-kslzdy8q 54 11 hydrazine hydrazine NN cord-033493-kslzdy8q 54 12 is be VBZ cord-033493-kslzdy8q 54 13 suggested suggest VBN cord-033493-kslzdy8q 54 14 to to TO cord-033493-kslzdy8q 54 15 proceed proceed VB cord-033493-kslzdy8q 54 16 via via IN cord-033493-kslzdy8q 54 17 initial initial JJ cord-033493-kslzdy8q 54 18 addition addition NN cord-033493-kslzdy8q 54 19 of of IN cord-033493-kslzdy8q 54 20 basic basic JJ cord-033493-kslzdy8q 54 21 nitrogen nitrogen NN cord-033493-kslzdy8q 54 22 in in IN cord-033493-kslzdy8q 54 23 hydrazine hydrazine NN cord-033493-kslzdy8q 54 24 to to IN cord-033493-kslzdy8q 54 25 the the DT cord-033493-kslzdy8q 54 26 double double JJ cord-033493-kslzdy8q 54 27 bond bond NN cord-033493-kslzdy8q 54 28 of of IN cord-033493-kslzdy8q 54 29 14 14 CD cord-033493-kslzdy8q 54 30 followed follow VBN cord-033493-kslzdy8q 54 31 by by IN cord-033493-kslzdy8q 54 32 the the DT cord-033493-kslzdy8q 54 33 formation formation NN cord-033493-kslzdy8q 54 34 of of IN cord-033493-kslzdy8q 54 35 the the DT cord-033493-kslzdy8q 54 36 adduct adduct NN cord-033493-kslzdy8q 54 37 15 15 CD cord-033493-kslzdy8q 54 38 and and CC cord-033493-kslzdy8q 54 39 elimination elimination NN cord-033493-kslzdy8q 54 40 of of IN cord-033493-kslzdy8q 54 41 ethyl ethyl NN cord-033493-kslzdy8q 54 42 cyanoacetate cyanoacetate NN cord-033493-kslzdy8q 54 43 . . . cord-033493-kslzdy8q 55 1 The the DT cord-033493-kslzdy8q 55 2 adduct adduct NN cord-033493-kslzdy8q 55 3 15 15 CD cord-033493-kslzdy8q 55 4 leads lead VBZ cord-033493-kslzdy8q 55 5 to to IN cord-033493-kslzdy8q 55 6 the the DT cord-033493-kslzdy8q 55 7 formation formation NN cord-033493-kslzdy8q 55 8 of of IN cord-033493-kslzdy8q 55 9 the the DT cord-033493-kslzdy8q 55 10 favored favor VBN cord-033493-kslzdy8q 55 11 , , , cord-033493-kslzdy8q 55 12 kinetically kinetically RB cord-033493-kslzdy8q 55 13 and and CC cord-033493-kslzdy8q 55 14 thermodynamically thermodynamically RB cord-033493-kslzdy8q 55 15 controlled control VBN cord-033493-kslzdy8q 55 16 3ethoxy-5-phenyl-1H-1,2,4-triazole 3ethoxy-5-phenyl-1h-1,2,4-triazole NN cord-033493-kslzdy8q 55 17 product product NN cord-033493-kslzdy8q 55 18 19 19 CD cord-033493-kslzdy8q 55 19 ( ( -LRB- cord-033493-kslzdy8q 55 20 Scheme scheme NN cord-033493-kslzdy8q 55 21 4 4 CD cord-033493-kslzdy8q 55 22 ) ) -RRB- cord-033493-kslzdy8q 55 23 . . . cord-033493-kslzdy8q 56 1 The the DT cord-033493-kslzdy8q 56 2 1 1 CD cord-033493-kslzdy8q 56 3 H h NN cord-033493-kslzdy8q 56 4 NMR nmr NN cord-033493-kslzdy8q 56 5 spectra spectra NN cord-033493-kslzdy8q 56 6 of of IN cord-033493-kslzdy8q 56 7 the the DT cord-033493-kslzdy8q 56 8 product product NN cord-033493-kslzdy8q 56 9 19 19 CD cord-033493-kslzdy8q 56 10 revealed reveal VBD cord-033493-kslzdy8q 56 11 the the DT cord-033493-kslzdy8q 56 12 presence presence NN cord-033493-kslzdy8q 56 13 of of IN cord-033493-kslzdy8q 56 14 an an DT cord-033493-kslzdy8q 56 15 ethoxy ethoxy JJ cord-033493-kslzdy8q 56 16 group group NN cord-033493-kslzdy8q 56 17 as as IN cord-033493-kslzdy8q 56 18 a a DT cord-033493-kslzdy8q 56 19 broad broad JJ cord-033493-kslzdy8q 56 20 singlet singlet NN cord-033493-kslzdy8q 56 21 at at IN cord-033493-kslzdy8q 56 22 δ1.37 δ1.37 CD cord-033493-kslzdy8q 56 23 ppm ppm NN cord-033493-kslzdy8q 56 24 assigned assign VBN cord-033493-kslzdy8q 56 25 to to IN cord-033493-kslzdy8q 56 26 the the DT cord-033493-kslzdy8q 56 27 CH CH NNP cord-033493-kslzdy8q 56 28 3 3 CD cord-033493-kslzdy8q 56 29 group group NN cord-033493-kslzdy8q 56 30 and and CC cord-033493-kslzdy8q 56 31 a a DT cord-033493-kslzdy8q 56 32 broad broad JJ cord-033493-kslzdy8q 56 33 singlet singlet NN cord-033493-kslzdy8q 56 34 at at IN cord-033493-kslzdy8q 56 35 δ δ NN cord-033493-kslzdy8q 56 36 4.34 4.34 CD cord-033493-kslzdy8q 56 37 ppm ppm NN cord-033493-kslzdy8q 56 38 assigned assign VBN cord-033493-kslzdy8q 56 39 to to IN cord-033493-kslzdy8q 56 40 the the DT cord-033493-kslzdy8q 56 41 CH CH NNP cord-033493-kslzdy8q 56 42 2 2 CD cord-033493-kslzdy8q 56 43 group group NN cord-033493-kslzdy8q 56 44 , , , cord-033493-kslzdy8q 56 45 a a DT cord-033493-kslzdy8q 56 46 multiplet multiplet NN cord-033493-kslzdy8q 56 47 at at IN cord-033493-kslzdy8q 56 48 δ δ NN cord-033493-kslzdy8q 56 49 7.47−7.93 7.47−7.93 CD cord-033493-kslzdy8q 56 50 ppm ppm NN cord-033493-kslzdy8q 56 51 assigned assign VBN cord-033493-kslzdy8q 56 52 to to IN cord-033493-kslzdy8q 56 53 the the DT cord-033493-kslzdy8q 56 54 phenyl phenyl NNP cord-033493-kslzdy8q 56 55 group group NN cord-033493-kslzdy8q 56 56 , , , cord-033493-kslzdy8q 56 57 and and CC cord-033493-kslzdy8q 56 58 a a DT cord-033493-kslzdy8q 56 59 triazole triazole NN cord-033493-kslzdy8q 56 60 ring ring NNP cord-033493-kslzdy8q 56 61 NH NH NNP cord-033493-kslzdy8q 56 62 at at IN cord-033493-kslzdy8q 56 63 δ δ NN cord-033493-kslzdy8q 56 64 13.72 13.72 CD cord-033493-kslzdy8q 56 65 ppm ppm NN cord-033493-kslzdy8q 56 66 . . . cord-033493-kslzdy8q 57 1 The the DT cord-033493-kslzdy8q 57 2 potassium potassium NN cord-033493-kslzdy8q 57 3 ethylenethiolate ethylenethiolate NN cord-033493-kslzdy8q 57 4 salts salt NNS cord-033493-kslzdy8q 57 5 2 2 CD cord-033493-kslzdy8q 57 6 and and CC cord-033493-kslzdy8q 57 7 13 13 CD cord-033493-kslzdy8q 57 8 reacted react VBD cord-033493-kslzdy8q 57 9 with with IN cord-033493-kslzdy8q 57 10 tetra tetra NN cord-033493-kslzdy8q 57 11 - - HYPH cord-033493-kslzdy8q 57 12 O o NN cord-033493-kslzdy8q 57 13 - - HYPH cord-033493-kslzdy8q 57 14 acetyl acetyl NN cord-033493-kslzdy8q 57 15 - - HYPH cord-033493-kslzdy8q 57 16 glucopyranosyl glucopyranosyl NN cord-033493-kslzdy8q 57 17 bromide bromide NN cord-033493-kslzdy8q 57 18 20 20 CD cord-033493-kslzdy8q 57 19 at at IN cord-033493-kslzdy8q 57 20 room room NN cord-033493-kslzdy8q 57 21 temperature temperature NN cord-033493-kslzdy8q 57 22 and and CC cord-033493-kslzdy8q 57 23 in in IN cord-033493-kslzdy8q 57 24 ethanol ethanol NN cord-033493-kslzdy8q 57 25 to to TO cord-033493-kslzdy8q 57 26 give give VB cord-033493-kslzdy8q 57 27 with with IN cord-033493-kslzdy8q 57 28 a a DT cord-033493-kslzdy8q 57 29 high high JJ cord-033493-kslzdy8q 57 30 yield yield NN cord-033493-kslzdy8q 57 31 the the DT cord-033493-kslzdy8q 57 32 corresponding correspond VBG cord-033493-kslzdy8q 57 33 Sglucosides sglucoside NNS cord-033493-kslzdy8q 57 34 21a 21a NNS cord-033493-kslzdy8q 57 35 , , , cord-033493-kslzdy8q 57 36 b b NN cord-033493-kslzdy8q 57 37 , , , cord-033493-kslzdy8q 57 38 respectively respectively RB cord-033493-kslzdy8q 57 39 . . . cord-033493-kslzdy8q 58 1 The the DT cord-033493-kslzdy8q 58 2 chemical chemical JJ cord-033493-kslzdy8q 58 3 structures structure NNS cord-033493-kslzdy8q 58 4 of of IN cord-033493-kslzdy8q 58 5 the the DT cord-033493-kslzdy8q 58 6 prepared prepared JJ cord-033493-kslzdy8q 58 7 compounds compound NNS cord-033493-kslzdy8q 58 8 21a 21a NNS cord-033493-kslzdy8q 58 9 , , , cord-033493-kslzdy8q 58 10 b b LS cord-033493-kslzdy8q 58 11 were be VBD cord-033493-kslzdy8q 58 12 confirmed confirm VBN cord-033493-kslzdy8q 58 13 by by IN cord-033493-kslzdy8q 58 14 elemental elemental JJ cord-033493-kslzdy8q 58 15 analyses analysis NNS cord-033493-kslzdy8q 58 16 and and CC cord-033493-kslzdy8q 58 17 spectroscopy spectroscopy NN cord-033493-kslzdy8q 58 18 ( ( -LRB- cord-033493-kslzdy8q 58 19 1 1 CD cord-033493-kslzdy8q 58 20 H h NN cord-033493-kslzdy8q 58 21 NMR nmr NN cord-033493-kslzdy8q 58 22 and and CC cord-033493-kslzdy8q 58 23 IR IR NNP cord-033493-kslzdy8q 58 24 ) ) -RRB- cord-033493-kslzdy8q 58 25 studies study NNS cord-033493-kslzdy8q 58 26 . . . cord-033493-kslzdy8q 59 1 For for IN cord-033493-kslzdy8q 59 2 example example NN cord-033493-kslzdy8q 59 3 , , , cord-033493-kslzdy8q 59 4 the the DT cord-033493-kslzdy8q 59 5 1 1 CD cord-033493-kslzdy8q 59 6 H h NN cord-033493-kslzdy8q 59 7 NMR nmr NN cord-033493-kslzdy8q 59 8 spectrum spectrum NN cord-033493-kslzdy8q 59 9 of of IN cord-033493-kslzdy8q 59 10 compound compound NN cord-033493-kslzdy8q 59 11 21b 21b NNS cord-033493-kslzdy8q 59 12 showed show VBD cord-033493-kslzdy8q 59 13 an an DT cord-033493-kslzdy8q 59 14 anomeric anomeric JJ cord-033493-kslzdy8q 59 15 proton proton NN cord-033493-kslzdy8q 59 16 at at IN cord-033493-kslzdy8q 59 17 δ δ NN cord-033493-kslzdy8q 60 1 6.10−6.12 6.10−6.12 CD cord-033493-kslzdy8q 60 2 ppm ppm NN cord-033493-kslzdy8q 60 3 as as IN cord-033493-kslzdy8q 60 4 a a DT cord-033493-kslzdy8q 60 5 doublet doublet NN cord-033493-kslzdy8q 60 6 , , , cord-033493-kslzdy8q 60 7 and and CC cord-033493-kslzdy8q 60 8 the the DT cord-033493-kslzdy8q 60 9 coupling coupling NN cord-033493-kslzdy8q 60 10 constant constant NN cord-033493-kslzdy8q 60 11 ( ( -LRB- cord-033493-kslzdy8q 60 12 J J NNP cord-033493-kslzdy8q 60 13 1′,2′ 1′,2′ CD cord-033493-kslzdy8q 60 14 = = SYM cord-033493-kslzdy8q 60 15 9.2 9.2 CD cord-033493-kslzdy8q 60 16 Hz Hz NNP cord-033493-kslzdy8q 60 17 ) ) -RRB- cord-033493-kslzdy8q 60 18 proved prove VBD cord-033493-kslzdy8q 61 1 H-1′to H-1′to NNS cord-033493-kslzdy8q 61 2 be be VB cord-033493-kslzdy8q 61 3 transdiaxial transdiaxial JJ cord-033493-kslzdy8q 61 4 to to IN cord-033493-kslzdy8q 61 5 H-2′. h-2′. NN cord-033493-kslzdy8q 61 6 45−50 45−50 CD cord-033493-kslzdy8q 62 1 The the DT cord-033493-kslzdy8q 62 2 signals signal NNS cord-033493-kslzdy8q 62 3 resonating resonate VBG cord-033493-kslzdy8q 62 4 at at IN cord-033493-kslzdy8q 62 5 3.92 3.92 CD cord-033493-kslzdy8q 62 6 , , , cord-033493-kslzdy8q 62 7 3.99 3.99 CD cord-033493-kslzdy8q 62 8 , , , cord-033493-kslzdy8q 62 9 4.04 4.04 CD cord-033493-kslzdy8q 62 10 , , , cord-033493-kslzdy8q 62 11 4.89 4.89 CD cord-033493-kslzdy8q 62 12 , , , cord-033493-kslzdy8q 62 13 5.03 5.03 CD cord-033493-kslzdy8q 62 14 , , , cord-033493-kslzdy8q 62 15 and and CC cord-033493-kslzdy8q 62 16 5.61 5.61 CD cord-033493-kslzdy8q 62 17 ppm ppm NN cord-033493-kslzdy8q 62 18 are be VBP cord-033493-kslzdy8q 62 19 assigned assign VBN cord-033493-kslzdy8q 62 20 to to IN cord-033493-kslzdy8q 62 21 six six CD cord-033493-kslzdy8q 62 22 glucose glucose NN cord-033493-kslzdy8q 62 23 protons proton NNS cord-033493-kslzdy8q 62 24 , , , cord-033493-kslzdy8q 62 25 and and CC cord-033493-kslzdy8q 62 26 the the DT cord-033493-kslzdy8q 62 27 four four CD cord-033493-kslzdy8q 62 28 singlets singlet NNS cord-033493-kslzdy8q 62 29 appearing appear VBG cord-033493-kslzdy8q 62 30 from from IN cord-033493-kslzdy8q 62 31 δ δ NN cord-033493-kslzdy8q 62 32 1.59 1.59 CD cord-033493-kslzdy8q 62 33 ppm ppm NN cord-033493-kslzdy8q 62 34 to to IN cord-033493-kslzdy8q 62 35 2.00 2.00 CD cord-033493-kslzdy8q 62 36 ppm ppm NN cord-033493-kslzdy8q 62 37 are be VBP cord-033493-kslzdy8q 62 38 assigned assign VBN cord-033493-kslzdy8q 62 39 to to IN cord-033493-kslzdy8q 62 40 four four CD cord-033493-kslzdy8q 62 41 acetyl acetyl NN cord-033493-kslzdy8q 62 42 groups group NNS cord-033493-kslzdy8q 62 43 . . . cord-033493-kslzdy8q 63 1 The the DT cord-033493-kslzdy8q 63 2 signal signal NN cord-033493-kslzdy8q 63 3 for for IN cord-033493-kslzdy8q 63 4 the the DT cord-033493-kslzdy8q 63 5 C-1′ C-1′ NNP cord-033493-kslzdy8q 63 6 atom atom NN cord-033493-kslzdy8q 63 7 in in IN cord-033493-kslzdy8q 63 8 the the DT cord-033493-kslzdy8q 63 9 13 13 CD cord-033493-kslzdy8q 63 10 C c NN cord-033493-kslzdy8q 63 11 NMR nmr NN cord-033493-kslzdy8q 63 12 spectrum spectrum NN cord-033493-kslzdy8q 63 13 of of IN cord-033493-kslzdy8q 63 14 21b 21b NNS cord-033493-kslzdy8q 63 15 appeared appear VBD cord-033493-kslzdy8q 63 16 at at IN cord-033493-kslzdy8q 63 17 δ δ NNP cord-033493-kslzdy8q 63 18 80.31 80.31 CD cord-033493-kslzdy8q 63 19 , , , cord-033493-kslzdy8q 63 20 and and CC cord-033493-kslzdy8q 63 21 the the DT cord-033493-kslzdy8q 63 22 signals signal NNS cord-033493-kslzdy8q 63 23 for for IN cord-033493-kslzdy8q 63 24 C-6′ C-6′ NNP cord-033493-kslzdy8q 63 25 , , , cord-033493-kslzdy8q 63 26 C-4′ C-4′ NNP cord-033493-kslzdy8q 63 27 , , , cord-033493-kslzdy8q 63 28 C-2′ c-2′ RB cord-033493-kslzdy8q 63 29 , , , cord-033493-kslzdy8q 63 30 C-3′ C-3′ NNP cord-033493-kslzdy8q 63 31 , , , cord-033493-kslzdy8q 63 32 and and CC cord-033493-kslzdy8q 63 33 C-5′ C-5′ NNP cord-033493-kslzdy8q 63 34 appeared appear VBD cord-033493-kslzdy8q 63 35 at at IN cord-033493-kslzdy8q 63 36 δ δ NN cord-033493-kslzdy8q 63 37 61.50 61.50 CD cord-033493-kslzdy8q 63 38 , , , cord-033493-kslzdy8q 63 39 68.76 68.76 CD cord-033493-kslzdy8q 63 40 , , , cord-033493-kslzdy8q 63 41 69.46 69.46 CD cord-033493-kslzdy8q 63 42 , , , cord-033493-kslzdy8q 63 43 73.47 73.47 CD cord-033493-kslzdy8q 63 44 , , , cord-033493-kslzdy8q 63 45 and and CC cord-033493-kslzdy8q 63 46 79.82 79.82 CD cord-033493-kslzdy8q 63 47 ppm ppm NN cord-033493-kslzdy8q 63 48 , , , cord-033493-kslzdy8q 63 49 respectively respectively RB cord-033493-kslzdy8q 63 50 . . . cord-033493-kslzdy8q 64 1 An an DT cord-033493-kslzdy8q 64 2 attempt attempt NN cord-033493-kslzdy8q 64 3 to to TO cord-033493-kslzdy8q 64 4 remove remove VB cord-033493-kslzdy8q 64 5 the the DT cord-033493-kslzdy8q 64 6 protection protection NN cord-033493-kslzdy8q 64 7 groups group NNS cord-033493-kslzdy8q 64 8 at at IN cord-033493-kslzdy8q 64 9 21 21 CD cord-033493-kslzdy8q 64 10 by by IN cord-033493-kslzdy8q 64 11 methanol−ammonia methanol−ammonia NNPS cord-033493-kslzdy8q 64 12 did do VBD cord-033493-kslzdy8q 64 13 not not RB cord-033493-kslzdy8q 64 14 result result VB cord-033493-kslzdy8q 64 15 in in IN cord-033493-kslzdy8q 64 16 the the DT cord-033493-kslzdy8q 64 17 formation formation NN cord-033493-kslzdy8q 64 18 of of IN cord-033493-kslzdy8q 64 19 the the DT cord-033493-kslzdy8q 64 20 corresponding correspond VBG cord-033493-kslzdy8q 64 21 free free JJ cord-033493-kslzdy8q 64 22 glycosides glycoside NNS cord-033493-kslzdy8q 64 23 . . . cord-033493-kslzdy8q 65 1 The the DT cord-033493-kslzdy8q 65 2 structure structure NN cord-033493-kslzdy8q 65 3 21 21 CD cord-033493-kslzdy8q 65 4 was be VBD cord-033493-kslzdy8q 65 5 suggested suggest VBN cord-033493-kslzdy8q 65 6 to to TO cord-033493-kslzdy8q 65 7 be be VB cord-033493-kslzdy8q 65 8 present present JJ cord-033493-kslzdy8q 65 9 in in IN cord-033493-kslzdy8q 65 10 the the DT cord-033493-kslzdy8q 65 11 E e NN cord-033493-kslzdy8q 65 12 form form NN cord-033493-kslzdy8q 65 13 and and CC cord-033493-kslzdy8q 65 14 not not RB cord-033493-kslzdy8q 65 15 in in IN cord-033493-kslzdy8q 65 16 the the DT cord-033493-kslzdy8q 65 17 Z z NN cord-033493-kslzdy8q 65 18 form form NN cord-033493-kslzdy8q 65 19 , , , cord-033493-kslzdy8q 65 20 which which WDT cord-033493-kslzdy8q 65 21 was be VBD cord-033493-kslzdy8q 65 22 demonstrated demonstrate VBN cord-033493-kslzdy8q 65 23 by by IN cord-033493-kslzdy8q 65 24 the the DT cord-033493-kslzdy8q 65 25 reaction reaction NN cord-033493-kslzdy8q 65 26 of of IN cord-033493-kslzdy8q 65 27 compounds compound NNS cord-033493-kslzdy8q 65 28 21 21 CD cord-033493-kslzdy8q 65 29 with with IN cord-033493-kslzdy8q 65 30 hydrazine hydrazine NN cord-033493-kslzdy8q 65 31 at at IN cord-033493-kslzdy8q 65 32 room room NN cord-033493-kslzdy8q 65 33 temperature temperature NN cord-033493-kslzdy8q 65 34 in in IN cord-033493-kslzdy8q 65 35 piperidine−ethanol piperidine−ethanol CD cord-033493-kslzdy8q 65 36 to to TO cord-033493-kslzdy8q 65 37 give give VB cord-033493-kslzdy8q 65 38 the the DT cord-033493-kslzdy8q 65 39 corresponding corresponding JJ cord-033493-kslzdy8q 65 40 5-aminoprazole 5-aminoprazole CD cord-033493-kslzdy8q 65 41 4 4 CD cord-033493-kslzdy8q 65 42 . . . cord-033493-kslzdy8q 66 1 The the DT cord-033493-kslzdy8q 66 2 structure structure NN cord-033493-kslzdy8q 66 3 of of IN cord-033493-kslzdy8q 66 4 4 4 CD cord-033493-kslzdy8q 66 5 was be VBD cord-033493-kslzdy8q 66 6 confirmed confirm VBN cord-033493-kslzdy8q 66 7 on on IN cord-033493-kslzdy8q 66 8 the the DT cord-033493-kslzdy8q 66 9 basis basis NN cord-033493-kslzdy8q 66 10 of of IN cord-033493-kslzdy8q 66 11 elemental elemental JJ cord-033493-kslzdy8q 66 12 analysis analysis NN cord-033493-kslzdy8q 66 13 and and CC cord-033493-kslzdy8q 66 14 spectral spectral JJ cord-033493-kslzdy8q 66 15 data datum NNS cord-033493-kslzdy8q 66 16 . . . cord-033493-kslzdy8q 67 1 Antiviral Antiviral NNP cord-033493-kslzdy8q 67 2 Activity Activity NNP cord-033493-kslzdy8q 67 3 . . . cord-033493-kslzdy8q 68 1 The the DT cord-033493-kslzdy8q 68 2 antiviral antiviral JJ cord-033493-kslzdy8q 68 3 activity activity NN cord-033493-kslzdy8q 68 4 was be VBD cord-033493-kslzdy8q 68 5 measured measure VBN cord-033493-kslzdy8q 68 6 for for IN cord-033493-kslzdy8q 68 7 the the DT cord-033493-kslzdy8q 68 8 synthesized synthesize VBN cord-033493-kslzdy8q 68 9 compounds compound NNS cord-033493-kslzdy8q 68 10 with with IN cord-033493-kslzdy8q 68 11 respect respect NN cord-033493-kslzdy8q 68 12 to to IN cord-033493-kslzdy8q 68 13 the the DT cord-033493-kslzdy8q 68 14 H5N1 H5N1 NNP cord-033493-kslzdy8q 68 15 influenza influenza NN cord-033493-kslzdy8q 68 16 virus virus NN cord-033493-kslzdy8q 68 17 strain strain VBP cord-033493-kslzdy8q 68 18 A a DT cord-033493-kslzdy8q 68 19 / / SYM cord-033493-kslzdy8q 68 20 Egypt Egypt NNP cord-033493-kslzdy8q 68 21 / / SYM cord-033493-kslzdy8q 68 22 M7217B/2013 M7217B/2013 NNP cord-033493-kslzdy8q 68 23 using use VBG cord-033493-kslzdy8q 68 24 MTT MTT NNP cord-033493-kslzdy8q 68 25 50 50 CD cord-033493-kslzdy8q 68 26 ) ) -RRB- cord-033493-kslzdy8q 68 27 and and CC cord-033493-kslzdy8q 68 28 plaque plaque NN cord-033493-kslzdy8q 68 29 reduction reduction NN cord-033493-kslzdy8q 68 30 assays assay NNS cord-033493-kslzdy8q 68 31 52 52 CD cord-033493-kslzdy8q 68 32 exploring explore VBG cord-033493-kslzdy8q 68 33 the the DT cord-033493-kslzdy8q 68 34 cytotoxicity cytotoxicity NN cord-033493-kslzdy8q 68 35 and and CC cord-033493-kslzdy8q 68 36 inhibition inhibition NN cord-033493-kslzdy8q 68 37 percentage percentage NN cord-033493-kslzdy8q 68 38 values value NNS cord-033493-kslzdy8q 68 39 , , , cord-033493-kslzdy8q 68 40 respectively respectively RB cord-033493-kslzdy8q 68 41 . . . cord-033493-kslzdy8q 69 1 The the DT cord-033493-kslzdy8q 69 2 anti anti JJ cord-033493-kslzdy8q 69 3 - - JJ cord-033493-kslzdy8q 69 4 influenza influenza JJ cord-033493-kslzdy8q 69 5 drug drug NN cord-033493-kslzdy8q 69 6 zanamivir zanamivir NNP cord-033493-kslzdy8q 69 7 was be VBD cord-033493-kslzdy8q 69 8 used use VBN cord-033493-kslzdy8q 69 9 as as IN cord-033493-kslzdy8q 69 10 a a DT cord-033493-kslzdy8q 69 11 positive positive JJ cord-033493-kslzdy8q 69 12 control control NN cord-033493-kslzdy8q 69 13 . . . cord-033493-kslzdy8q 70 1 53 53 CD cord-033493-kslzdy8q 70 2 Antiviral antiviral JJ cord-033493-kslzdy8q 70 3 bioassay bioassay NN cord-033493-kslzdy8q 70 4 data datum NNS cord-033493-kslzdy8q 70 5 ( ( -LRB- cord-033493-kslzdy8q 70 6 see see VB cord-033493-kslzdy8q 70 7 Table table NN cord-033493-kslzdy8q 70 8 1 1 CD cord-033493-kslzdy8q 70 9 and and CC cord-033493-kslzdy8q 70 10 Figure figure NN cord-033493-kslzdy8q 70 11 4 4 CD cord-033493-kslzdy8q 70 12 ) ) -RRB- cord-033493-kslzdy8q 70 13 indicated indicate VBD cord-033493-kslzdy8q 70 14 that that IN cord-033493-kslzdy8q 70 15 most most JJS cord-033493-kslzdy8q 70 16 of of IN cord-033493-kslzdy8q 70 17 the the DT cord-033493-kslzdy8q 70 18 compounds compound NNS cord-033493-kslzdy8q 70 19 demonstrated demonstrate VBD cord-033493-kslzdy8q 70 20 a a DT cord-033493-kslzdy8q 70 21 dosedependent dosedependent NN cord-033493-kslzdy8q 70 22 inhibition inhibition NN cord-033493-kslzdy8q 70 23 behavior behavior NN cord-033493-kslzdy8q 70 24 . . . cord-033493-kslzdy8q 71 1 Based base VBN cord-033493-kslzdy8q 71 2 on on IN cord-033493-kslzdy8q 71 3 the the DT cord-033493-kslzdy8q 71 4 U.S. U.S. NNP cord-033493-kslzdy8q 71 5 National National NNP cord-033493-kslzdy8q 71 6 Cancer Cancer NNP cord-033493-kslzdy8q 71 7 Institute Institute NNP cord-033493-kslzdy8q 71 8 ( ( -LRB- cord-033493-kslzdy8q 71 9 NCI NCI NNP cord-033493-kslzdy8q 71 10 ) ) -RRB- cord-033493-kslzdy8q 71 11 and and CC cord-033493-kslzdy8q 71 12 GERAN GERAN NNP cord-033493-kslzdy8q 71 13 protocol protocol NN cord-033493-kslzdy8q 71 14 , , , cord-033493-kslzdy8q 71 15 54,55 54,55 CD cord-033493-kslzdy8q 71 16 the the DT cord-033493-kslzdy8q 71 17 LD LD NNP cord-033493-kslzdy8q 71 18 50 50 CD cord-033493-kslzdy8q 71 19 values value NNS cord-033493-kslzdy8q 71 20 indicate indicate VBP cord-033493-kslzdy8q 71 21 that that IN cord-033493-kslzdy8q 71 22 most most RBS cord-033493-kslzdy8q 71 23 tested test VBN cord-033493-kslzdy8q 71 24 compounds compound NNS cord-033493-kslzdy8q 71 25 , , , cord-033493-kslzdy8q 71 26 especially especially RB cord-033493-kslzdy8q 71 27 compound compound NN cord-033493-kslzdy8q 71 28 3b 3b NNS cord-033493-kslzdy8q 71 29 , , , cord-033493-kslzdy8q 71 30 are be VBP cord-033493-kslzdy8q 71 31 safe safe JJ cord-033493-kslzdy8q 71 32 for for IN cord-033493-kslzdy8q 71 33 healthy healthy JJ cord-033493-kslzdy8q 71 34 cells cell NNS cord-033493-kslzdy8q 71 35 , , , cord-033493-kslzdy8q 71 36 while while IN cord-033493-kslzdy8q 71 37 the the DT cord-033493-kslzdy8q 71 38 plaque plaque NN cord-033493-kslzdy8q 71 39 reduction reduction NN cord-033493-kslzdy8q 71 40 assay assay NN cord-033493-kslzdy8q 71 41 showed show VBD cord-033493-kslzdy8q 71 42 that that IN cord-033493-kslzdy8q 71 43 compounds compound NNS cord-033493-kslzdy8q 71 44 3b 3b CD cord-033493-kslzdy8q 71 45 , , , cord-033493-kslzdy8q 71 46 4 4 CD cord-033493-kslzdy8q 71 47 , , , cord-033493-kslzdy8q 71 48 and and CC cord-033493-kslzdy8q 71 49 10b 10b NNS cord-033493-kslzdy8q 71 50 have have VBP cord-033493-kslzdy8q 71 51 higher high JJR cord-033493-kslzdy8q 71 52 therapeutic therapeutic JJ cord-033493-kslzdy8q 71 53 indices index NNS cord-033493-kslzdy8q 71 54 compared compare VBN cord-033493-kslzdy8q 71 55 to to IN cord-033493-kslzdy8q 71 56 the the DT cord-033493-kslzdy8q 71 57 other other JJ cord-033493-kslzdy8q 71 58 synthesized synthesize VBN cord-033493-kslzdy8q 71 59 compounds compound NNS cord-033493-kslzdy8q 71 60 . . . cord-033493-kslzdy8q 72 1 In in IN cord-033493-kslzdy8q 72 2 particular particular JJ cord-033493-kslzdy8q 72 3 , , , cord-033493-kslzdy8q 72 4 compound compound NN cord-033493-kslzdy8q 72 5 3b 3b CD cord-033493-kslzdy8q 72 6 exhibited exhibit VBD cord-033493-kslzdy8q 72 7 the the DT cord-033493-kslzdy8q 72 8 highest high JJS cord-033493-kslzdy8q 72 9 antiviral antiviral JJ cord-033493-kslzdy8q 72 10 activity activity NN cord-033493-kslzdy8q 72 11 at at IN cord-033493-kslzdy8q 72 12 the the DT cord-033493-kslzdy8q 72 13 given give VBN cord-033493-kslzdy8q 72 14 concentrations concentration NNS cord-033493-kslzdy8q 72 15 with with IN cord-033493-kslzdy8q 72 16 percentage percentage NN cord-033493-kslzdy8q 72 17 of of IN cord-033493-kslzdy8q 72 18 virus virus NN cord-033493-kslzdy8q 72 19 reduction reduction NN cord-033493-kslzdy8q 72 20 reaching reach VBG cord-033493-kslzdy8q 72 21 85 85 CD cord-033493-kslzdy8q 72 22 % % NN cord-033493-kslzdy8q 72 23 at at IN cord-033493-kslzdy8q 72 24 a a DT cord-033493-kslzdy8q 72 25 concentration concentration NN cord-033493-kslzdy8q 72 26 of of IN cord-033493-kslzdy8q 72 27 0.25 0.25 CD cord-033493-kslzdy8q 72 28 μmol/ μmol/ NNS cord-033493-kslzdy8q 72 29 ml ml NN cord-033493-kslzdy8q 72 30 . . . cord-033493-kslzdy8q 73 1 On on IN cord-033493-kslzdy8q 73 2 the the DT cord-033493-kslzdy8q 73 3 other other JJ cord-033493-kslzdy8q 73 4 hand hand NN cord-033493-kslzdy8q 73 5 , , , cord-033493-kslzdy8q 73 6 compounds compound NNS cord-033493-kslzdy8q 73 7 3c 3c NNP cord-033493-kslzdy8q 73 8 , , , cord-033493-kslzdy8q 73 9 10c 10c CD cord-033493-kslzdy8q 73 10 , , , cord-033493-kslzdy8q 73 11 12a 12a NNS cord-033493-kslzdy8q 73 12 , , , cord-033493-kslzdy8q 73 13 19 19 CD cord-033493-kslzdy8q 73 14 , , , cord-033493-kslzdy8q 73 15 21a 21a NNS cord-033493-kslzdy8q 73 16 , , , cord-033493-kslzdy8q 73 17 and and CC cord-033493-kslzdy8q 73 18 21b 21b NNS cord-033493-kslzdy8q 73 19 demonstrated demonstrate VBD cord-033493-kslzdy8q 73 20 a a DT cord-033493-kslzdy8q 73 21 moderate moderate JJ cord-033493-kslzdy8q 73 22 anti anti JJ cord-033493-kslzdy8q 73 23 - - JJ cord-033493-kslzdy8q 73 24 H5N1 h5n1 JJ cord-033493-kslzdy8q 73 25 activity activity NN cord-033493-kslzdy8q 73 26 with with IN cord-033493-kslzdy8q 73 27 viral viral JJ cord-033493-kslzdy8q 73 28 inhibition inhibition NN cord-033493-kslzdy8q 73 29 over over IN cord-033493-kslzdy8q 73 30 65 65 CD cord-033493-kslzdy8q 73 31 percent percent NN cord-033493-kslzdy8q 73 32 . . . cord-033493-kslzdy8q 74 1 In in IN cord-033493-kslzdy8q 74 2 general general JJ cord-033493-kslzdy8q 74 3 , , , cord-033493-kslzdy8q 74 4 it -PRON- PRP cord-033493-kslzdy8q 74 5 has have VBZ cord-033493-kslzdy8q 74 6 been be VBN cord-033493-kslzdy8q 74 7 observed observe VBN cord-033493-kslzdy8q 74 8 that that IN cord-033493-kslzdy8q 74 9 compound compound NN cord-033493-kslzdy8q 74 10 3b 3b CD cord-033493-kslzdy8q 74 11 with with IN cord-033493-kslzdy8q 74 12 an an DT cord-033493-kslzdy8q 74 13 ethylthio ethylthio JJ cord-033493-kslzdy8q 74 14 group group NN cord-033493-kslzdy8q 74 15 at at IN cord-033493-kslzdy8q 74 16 a a DT cord-033493-kslzdy8q 74 17 concentration concentration NN cord-033493-kslzdy8q 74 18 of of IN cord-033493-kslzdy8q 74 19 0.25 0.25 CD cord-033493-kslzdy8q 74 20 μmol μmol NNP cord-033493-kslzdy8q 74 21 / / SYM cord-033493-kslzdy8q 74 22 ml ml NNP cord-033493-kslzdy8q 74 23 was be VBD cord-033493-kslzdy8q 74 24 more more RBR cord-033493-kslzdy8q 74 25 active active JJ cord-033493-kslzdy8q 74 26 compared compare VBN cord-033493-kslzdy8q 74 27 to to IN cord-033493-kslzdy8q 74 28 3a 3a CD cord-033493-kslzdy8q 74 29 and and CC cord-033493-kslzdy8q 74 30 3c 3c NNP cord-033493-kslzdy8q 74 31 with with IN cord-033493-kslzdy8q 74 32 methylthio methylthio NNP cord-033493-kslzdy8q 74 33 and and CC cord-033493-kslzdy8q 74 34 benzylthio benzylthio NNP cord-033493-kslzdy8q 74 35 groups group NNS cord-033493-kslzdy8q 74 36 , , , cord-033493-kslzdy8q 74 37 respectively respectively RB cord-033493-kslzdy8q 74 38 . . . cord-033493-kslzdy8q 75 1 Additionally additionally RB cord-033493-kslzdy8q 75 2 , , , cord-033493-kslzdy8q 75 3 conversion conversion NN cord-033493-kslzdy8q 75 4 of of IN cord-033493-kslzdy8q 75 5 N-(2,2-dicyano-1-(alkylthio)vinyl)benzamides N-(2,2-dicyano-1-(alkylthio)vinyl)benzamides NNP cord-033493-kslzdy8q 75 6 3a 3a NNP cord-033493-kslzdy8q 75 7 and and CC cord-033493-kslzdy8q 75 8 3c 3c NNP cord-033493-kslzdy8q 75 9 to to IN cord-033493-kslzdy8q 75 10 the the DT cord-033493-kslzdy8q 75 11 5-aminopyrazole 5-aminopyrazole CD cord-033493-kslzdy8q 75 12 4 4 CD cord-033493-kslzdy8q 75 13 relatively relatively RB cord-033493-kslzdy8q 75 14 enhanced enhance VBD cord-033493-kslzdy8q 75 15 the the DT cord-033493-kslzdy8q 75 16 activity activity NN cord-033493-kslzdy8q 75 17 at at IN cord-033493-kslzdy8q 75 18 the the DT cord-033493-kslzdy8q 75 19 same same JJ cord-033493-kslzdy8q 75 20 concentration concentration NN cord-033493-kslzdy8q 75 21 . . . cord-033493-kslzdy8q 76 1 The the DT cord-033493-kslzdy8q 76 2 presence presence NN cord-033493-kslzdy8q 76 3 of of IN cord-033493-kslzdy8q 76 4 pyrazolotriazine pyrazolotriazine NN cord-033493-kslzdy8q 76 5 moieties moiety NNS cord-033493-kslzdy8q 76 6 in in IN cord-033493-kslzdy8q 76 7 compounds compound NNS cord-033493-kslzdy8q 76 8 6a 6a NNP cord-033493-kslzdy8q 76 9 , , , cord-033493-kslzdy8q 76 10 b b NN cord-033493-kslzdy8q 76 11 decreases decrease VBZ cord-033493-kslzdy8q 76 12 the the DT cord-033493-kslzdy8q 76 13 activity activity NN cord-033493-kslzdy8q 76 14 compared compare VBN cord-033493-kslzdy8q 76 15 to to IN cord-033493-kslzdy8q 76 16 the the DT cord-033493-kslzdy8q 76 17 5-aminopyrazole 5-aminopyrazole CD cord-033493-kslzdy8q 76 18 4 4 CD cord-033493-kslzdy8q 76 19 . . . cord-033493-kslzdy8q 77 1 Compound compound NN cord-033493-kslzdy8q 77 2 10b 10b NNS cord-033493-kslzdy8q 77 3 with with IN cord-033493-kslzdy8q 77 4 a a DT cord-033493-kslzdy8q 77 5 pyrazolo[1,5-a]pyrimidine pyrazolo[1,5-a]pyrimidine JJ cord-033493-kslzdy8q 77 6 scaffold scaffold NN cord-033493-kslzdy8q 77 7 and and CC cord-033493-kslzdy8q 77 8 amino- amino- NN cord-033493-kslzdy8q 77 9 , , , cord-033493-kslzdy8q 77 10 cyano- cyano- JJ cord-033493-kslzdy8q 77 11 , , , cord-033493-kslzdy8q 77 12 and and CC cord-033493-kslzdy8q 77 13 methoxy methoxy JJ cord-033493-kslzdy8q 77 14 phenyl phenyl NN cord-033493-kslzdy8q 77 15 groups group NNS cord-033493-kslzdy8q 77 16 was be VBD cord-033493-kslzdy8q 77 17 found find VBN cord-033493-kslzdy8q 77 18 to to TO cord-033493-kslzdy8q 77 19 have have VB cord-033493-kslzdy8q 77 20 the the DT cord-033493-kslzdy8q 77 21 highest high JJS cord-033493-kslzdy8q 77 22 potency potency NN cord-033493-kslzdy8q 77 23 in in IN cord-033493-kslzdy8q 77 24 the the DT cord-033493-kslzdy8q 77 25 series series NN cord-033493-kslzdy8q 77 26 at at IN cord-033493-kslzdy8q 77 27 a a DT cord-033493-kslzdy8q 77 28 concentration concentration NN cord-033493-kslzdy8q 77 29 of of IN cord-033493-kslzdy8q 77 30 0.125 0.125 CD cord-033493-kslzdy8q 77 31 μmol μmol NNP cord-033493-kslzdy8q 77 32 / / SYM cord-033493-kslzdy8q 77 33 ml ml NN cord-033493-kslzdy8q 77 34 ( ( -LRB- cord-033493-kslzdy8q 77 35 83 83 CD cord-033493-kslzdy8q 77 36 % % NN cord-033493-kslzdy8q 77 37 ) ) -RRB- cord-033493-kslzdy8q 77 38 . . . cord-033493-kslzdy8q 78 1 Unexpectedly unexpectedly RB cord-033493-kslzdy8q 78 2 , , , cord-033493-kslzdy8q 78 3 the the DT cord-033493-kslzdy8q 78 4 synthesis synthesis NN cord-033493-kslzdy8q 78 5 of of IN cord-033493-kslzdy8q 78 6 derivatives derivative NNS cord-033493-kslzdy8q 78 7 ( ( -LRB- cord-033493-kslzdy8q 78 8 21a 21a NNS cord-033493-kslzdy8q 78 9 and and CC cord-033493-kslzdy8q 78 10 21b 21b NNS cord-033493-kslzdy8q 78 11 ) ) -RRB- cord-033493-kslzdy8q 78 12 with with IN cord-033493-kslzdy8q 78 13 a a DT cord-033493-kslzdy8q 78 14 sugar sugar NN cord-033493-kslzdy8q 78 15 moiety moiety NN cord-033493-kslzdy8q 78 16 had have VBD cord-033493-kslzdy8q 78 17 no no DT cord-033493-kslzdy8q 78 18 significant significant JJ cord-033493-kslzdy8q 78 19 effect effect NN cord-033493-kslzdy8q 78 20 on on IN cord-033493-kslzdy8q 78 21 the the DT cord-033493-kslzdy8q 78 22 antiviral antiviral JJ cord-033493-kslzdy8q 78 23 activity activity NN cord-033493-kslzdy8q 78 24 ( ( -LRB- cord-033493-kslzdy8q 78 25 Scheme scheme NN cord-033493-kslzdy8q 78 26 5 5 CD cord-033493-kslzdy8q 78 27 ) ) -RRB- cord-033493-kslzdy8q 78 28 , , , cord-033493-kslzdy8q 78 29 where where WRB cord-033493-kslzdy8q 78 30 the the DT cord-033493-kslzdy8q 78 31 study study NN cord-033493-kslzdy8q 78 32 showed show VBD cord-033493-kslzdy8q 78 33 that that IN cord-033493-kslzdy8q 78 34 N-(2,2-dicyano-1-(alkylthio)vinyl)benzamide N-(2,2-dicyano-1-(alkylthio)vinyl)benzamide NNP cord-033493-kslzdy8q 78 35 3b 3b CD cord-033493-kslzdy8q 78 36 with with IN cord-033493-kslzdy8q 78 37 S S NNP cord-033493-kslzdy8q 78 38 - - HYPH cord-033493-kslzdy8q 78 39 ethyl ethyl NNP cord-033493-kslzdy8q 78 40 seemed seem VBD cord-033493-kslzdy8q 78 41 to to TO cord-033493-kslzdy8q 78 42 be be VB cord-033493-kslzdy8q 78 43 more more RBR cord-033493-kslzdy8q 78 44 active active JJ cord-033493-kslzdy8q 78 45 than than IN cord-033493-kslzdy8q 78 46 the the DT cord-033493-kslzdy8q 78 47 corresponding correspond VBG cord-033493-kslzdy8q 78 48 derivatives derivative NNS cord-033493-kslzdy8q 78 49 of of IN cord-033493-kslzdy8q 78 50 acyclic acyclic JJ cord-033493-kslzdy8q 78 51 thioglucosides thioglucoside NNS cord-033493-kslzdy8q 78 52 21a 21a NNS cord-033493-kslzdy8q 78 53 , , , cord-033493-kslzdy8q 79 1 b. b. NNP cord-033493-kslzdy8q 80 1 Synthesis Synthesis NNP cord-033493-kslzdy8q 80 2 of of IN cord-033493-kslzdy8q 80 3 N-(5-amino-3,6-dicyano-7-arylpyrazolo[1,5a]pyrimidin-2-yl)benzamides N-(5-amino-3,6-dicyano-7-arylpyrazolo[1,5a]pyrimidin-2-yl)benzamides NNP cord-033493-kslzdy8q 80 4 10a−c 10a−c CD cord-033493-kslzdy8q 80 5 . . . cord-033493-kslzdy8q 81 1 Method method NN cord-033493-kslzdy8q 81 2 : : : cord-033493-kslzdy8q 81 3 a a DT cord-033493-kslzdy8q 81 4 mixture mixture NN cord-033493-kslzdy8q 81 5 of of IN cord-033493-kslzdy8q 81 6 compound compound NN cord-033493-kslzdy8q 81 7 4 4 CD cord-033493-kslzdy8q 81 8 ( ( -LRB- cord-033493-kslzdy8q 81 9 2.27 2.27 CD cord-033493-kslzdy8q 81 10 g g NN cord-033493-kslzdy8q 81 11 , , , cord-033493-kslzdy8q 81 12 0.01 0.01 CD cord-033493-kslzdy8q 81 13 mol mol NN cord-033493-kslzdy8q 81 14 ) ) -RRB- cord-033493-kslzdy8q 81 15 and and CC cord-033493-kslzdy8q 81 16 benzylidene benzylidene JJ cord-033493-kslzdy8q 81 17 propane propane NN cord-033493-kslzdy8q 81 18 - - HYPH cord-033493-kslzdy8q 81 19 dinitrile dinitrile NN cord-033493-kslzdy8q 81 20 9a 9a NN cord-033493-kslzdy8q 81 21 ( ( -LRB- cord-033493-kslzdy8q 81 22 1.54 1.54 CD cord-033493-kslzdy8q 81 23 g g NN cord-033493-kslzdy8q 81 24 , , , cord-033493-kslzdy8q 81 25 0.01 0.01 CD cord-033493-kslzdy8q 81 26 mol mol NN cord-033493-kslzdy8q 81 27 ) ) -RRB- cord-033493-kslzdy8q 81 28 , , , cord-033493-kslzdy8q 81 29 ( ( -LRB- cord-033493-kslzdy8q 81 30 4-methoxy 4-methoxy CD cord-033493-kslzdy8q 81 31 benzylidene benzylidene NN cord-033493-kslzdy8q 81 32 ) ) -RRB- cord-033493-kslzdy8q 82 1 propanedinitrile propanedinitrile NNP cord-033493-kslzdy8q 82 2 9b 9b NNP cord-033493-kslzdy8q 82 3 ( ( -LRB- cord-033493-kslzdy8q 82 4 1.84 1.84 CD cord-033493-kslzdy8q 82 5 g g NN cord-033493-kslzdy8q 82 6 , , , cord-033493-kslzdy8q 82 7 0.01 0.01 CD cord-033493-kslzdy8q 82 8 mol mol NN cord-033493-kslzdy8q 82 9 ) ) -RRB- cord-033493-kslzdy8q 82 10 , , , cord-033493-kslzdy8q 82 11 or or CC cord-033493-kslzdy8q 82 12 ( ( -LRB- cord-033493-kslzdy8q 82 13 4-chlorobenzylidene 4-chlorobenzylidene CD cord-033493-kslzdy8q 82 14 ) ) -RRB- cord-033493-kslzdy8q 82 15 propanedinitrile propanedinitrile NNP cord-033493-kslzdy8q 82 16 9c 9c NNP cord-033493-kslzdy8q 82 17 ( ( -LRB- cord-033493-kslzdy8q 82 18 1.88 1.88 CD cord-033493-kslzdy8q 82 19 g g NN cord-033493-kslzdy8q 82 20 , , , cord-033493-kslzdy8q 82 21 0.01 0.01 CD cord-033493-kslzdy8q 82 22 mol mol NN cord-033493-kslzdy8q 82 23 ) ) -RRB- cord-033493-kslzdy8q 83 1 was be VBD cord-033493-kslzdy8q 83 2 refluxed refluxe VBN cord-033493-kslzdy8q 83 3 for for IN cord-033493-kslzdy8q 83 4 5 5 CD cord-033493-kslzdy8q 83 5 h h NN cord-033493-kslzdy8q 83 6 in in IN cord-033493-kslzdy8q 83 7 ethanol ethanol NN cord-033493-kslzdy8q 83 8 ( ( -LRB- cord-033493-kslzdy8q 83 9 20 20 CD cord-033493-kslzdy8q 83 10 mL ml NN cord-033493-kslzdy8q 83 11 ) ) -RRB- cord-033493-kslzdy8q 83 12 containing contain VBG cord-033493-kslzdy8q 83 13 drops drop NNS cord-033493-kslzdy8q 83 14 of of IN cord-033493-kslzdy8q 83 15 piperidine piperidine NN cord-033493-kslzdy8q 83 16 . . . cord-033493-kslzdy8q 84 1 The the DT cord-033493-kslzdy8q 84 2 reaction reaction NN cord-033493-kslzdy8q 84 3 mixture mixture NN cord-033493-kslzdy8q 84 4 was be VBD cord-033493-kslzdy8q 84 5 allowed allow VBN cord-033493-kslzdy8q 84 6 to to TO cord-033493-kslzdy8q 84 7 cool cool VB cord-033493-kslzdy8q 84 8 to to IN cord-033493-kslzdy8q 84 9 room room NN cord-033493-kslzdy8q 84 10 temperature temperature NN cord-033493-kslzdy8q 84 11 . . . cord-033493-kslzdy8q 85 1 The the DT cord-033493-kslzdy8q 85 2 precipitate precipitate NN cord-033493-kslzdy8q 85 3 was be VBD cord-033493-kslzdy8q 85 4 collected collect VBN cord-033493-kslzdy8q 85 5 by by IN cord-033493-kslzdy8q 85 6 filtration filtration NN cord-033493-kslzdy8q 85 7 and and CC cord-033493-kslzdy8q 85 8 crystallized crystallize VBN cord-033493-kslzdy8q 85 9 from from IN cord-033493-kslzdy8q 85 10 DMF DMF NNP cord-033493-kslzdy8q 85 11 . . . cord-033493-kslzdy8q 86 1 N-(5-Amino-3,6-dicyano-7-phenylpyrazolo[1,5-a]pyrimidin-2-yl)benzamide n-(5-amino-3,6-dicyano-7-phenylpyrazolo[1,5-a]pyrimidin-2-yl)benzamide RB cord-033493-kslzdy8q 86 2 10a 10a NNS cord-033493-kslzdy8q 86 3 . . . cord-033493-kslzdy8q 87 1 Yellow yellow JJ cord-033493-kslzdy8q 87 2 powder powder NN cord-033493-kslzdy8q 87 3 ; ; , cord-033493-kslzdy8q 87 4 ( ( -LRB- cord-033493-kslzdy8q 87 5 DMF DMF NNP cord-033493-kslzdy8q 87 6 ) ) -RRB- cord-033493-kslzdy8q 87 7 ; ; : cord-033493-kslzdy8q 87 8 yield yield VBP cord-033493-kslzdy8q 87 9 55 55 CD cord-033493-kslzdy8q 87 10 % % NN cord-033493-kslzdy8q 87 11 ; ; , cord-033493-kslzdy8q 87 12 mp>300 mp>300 JJ cord-033493-kslzdy8q 87 13 ° ° NN cord-033493-kslzdy8q 87 14 C c NN cord-033493-kslzdy8q 87 15 ; ; : cord-033493-kslzdy8q 87 16 1 1 CD cord-033493-kslzdy8q 87 17 Synthesis Synthesis NNP cord-033493-kslzdy8q 87 18 of of IN cord-033493-kslzdy8q 87 19 ( ( -LRB- cord-033493-kslzdy8q 87 20 E)-Ethyl E)-Ethyl NNP cord-033493-kslzdy8q 87 21 3-benzamido-2-cyano-3-(methylthio)acrylate 3-benzamido-2-cyano-3-(methylthio)acrylate CD cord-033493-kslzdy8q 87 22 14 14 CD cord-033493-kslzdy8q 87 23 . . . cord-033493-kslzdy8q 88 1 Method method NN cord-033493-kslzdy8q 88 2 : : : cord-033493-kslzdy8q 88 3 a a DT cord-033493-kslzdy8q 88 4 mixture mixture NN cord-033493-kslzdy8q 88 5 of of IN cord-033493-kslzdy8q 88 6 ethyl ethyl NN cord-033493-kslzdy8q 88 7 cyanoacetate cyanoacetate NN cord-033493-kslzdy8q 88 8 ( ( -LRB- cord-033493-kslzdy8q 88 9 1.13 1.13 CD cord-033493-kslzdy8q 88 10 g g NN cord-033493-kslzdy8q 88 11 , , , cord-033493-kslzdy8q 88 12 0.01 0.01 CD cord-033493-kslzdy8q 88 13 mol mol NN cord-033493-kslzdy8q 88 14 ) ) -RRB- cord-033493-kslzdy8q 88 15 and and CC cord-033493-kslzdy8q 88 16 benzoyl benzoyl NN cord-033493-kslzdy8q 88 17 isothiocyanate isothiocyanate NN cord-033493-kslzdy8q 88 18 ( ( -LRB- cord-033493-kslzdy8q 88 19 1.63 1.63 CD cord-033493-kslzdy8q 88 20 g g NN cord-033493-kslzdy8q 88 21 , , , cord-033493-kslzdy8q 88 22 0.01 0.01 CD cord-033493-kslzdy8q 88 23 mol mol NN cord-033493-kslzdy8q 88 24 ) ) -RRB- cord-033493-kslzdy8q 88 25 was be VBD cord-033493-kslzdy8q 88 26 heated heat VBN cord-033493-kslzdy8q 88 27 for for IN cord-033493-kslzdy8q 88 28 30 30 CD cord-033493-kslzdy8q 88 29 min min NN cord-033493-kslzdy8q 88 30 in in IN cord-033493-kslzdy8q 88 31 ethanol ethanol NN cord-033493-kslzdy8q 88 32 ( ( -LRB- cord-033493-kslzdy8q 88 33 25 25 CD cord-033493-kslzdy8q 88 34 mL ml NN cord-033493-kslzdy8q 88 35 ) ) -RRB- cord-033493-kslzdy8q 88 36 in in IN cord-033493-kslzdy8q 88 37 the the DT cord-033493-kslzdy8q 88 38 presence presence NN cord-033493-kslzdy8q 88 39 of of IN cord-033493-kslzdy8q 88 40 potassium potassium NN cord-033493-kslzdy8q 88 41 hydroxide hydroxide NN cord-033493-kslzdy8q 88 42 ( ( -LRB- cord-033493-kslzdy8q 88 43 0.56 0.56 CD cord-033493-kslzdy8q 88 44 g g NN cord-033493-kslzdy8q 88 45 , , , cord-033493-kslzdy8q 88 46 0.01 0.01 CD cord-033493-kslzdy8q 88 47 mol mol NN cord-033493-kslzdy8q 88 48 ) ) -RRB- cord-033493-kslzdy8q 88 49 . . . cord-033493-kslzdy8q 89 1 After after IN cord-033493-kslzdy8q 89 2 cooling cool VBG cord-033493-kslzdy8q 89 3 , , , cord-033493-kslzdy8q 89 4 methyl methyl NN cord-033493-kslzdy8q 89 5 iodide iodide NN cord-033493-kslzdy8q 89 6 ( ( -LRB- cord-033493-kslzdy8q 89 7 1 1 CD cord-033493-kslzdy8q 89 8 mmol mmol JJ cord-033493-kslzdy8q 89 9 ) ) -RRB- cord-033493-kslzdy8q 89 10 was be VBD cord-033493-kslzdy8q 89 11 added add VBN cord-033493-kslzdy8q 89 12 , , , cord-033493-kslzdy8q 89 13 and and CC cord-033493-kslzdy8q 89 14 the the DT cord-033493-kslzdy8q 89 15 mixture mixture NN cord-033493-kslzdy8q 89 16 was be VBD cord-033493-kslzdy8q 89 17 stirred stir VBN cord-033493-kslzdy8q 89 18 overnight overnight RB cord-033493-kslzdy8q 89 19 . . . cord-033493-kslzdy8q 90 1 The the DT cord-033493-kslzdy8q 90 2 resulting result VBG cord-033493-kslzdy8q 90 3 solid solid JJ cord-033493-kslzdy8q 90 4 product product NN cord-033493-kslzdy8q 90 5 was be VBD cord-033493-kslzdy8q 90 6 collected collect VBN cord-033493-kslzdy8q 90 7 by by IN cord-033493-kslzdy8q 90 8 filtration filtration NN cord-033493-kslzdy8q 90 9 and and CC cord-033493-kslzdy8q 90 10 recrystallized recrystallize VBN cord-033493-kslzdy8q 90 11 from from IN cord-033493-kslzdy8q 90 12 ethanol ethanol NN cord-033493-kslzdy8q 90 13 . . . cord-033493-kslzdy8q 91 1 MTT MTT NNP cord-033493-kslzdy8q 91 2 Cytotoxicity Cytotoxicity NNP cord-033493-kslzdy8q 91 3 Assay Assay NNP cord-033493-kslzdy8q 91 4 ( ( -LRB- cord-033493-kslzdy8q 91 5 LD LD NNP cord-033493-kslzdy8q 91 6 50 50 CD cord-033493-kslzdy8q 91 7 ) ) -RRB- cord-033493-kslzdy8q 91 8 . . . cord-033493-kslzdy8q 92 1 The the DT cord-033493-kslzdy8q 92 2 samples sample NNS cord-033493-kslzdy8q 92 3 were be VBD cord-033493-kslzdy8q 92 4 diluted dilute VBN cord-033493-kslzdy8q 92 5 to to IN cord-033493-kslzdy8q 92 6 10-fold 10-fold CD cord-033493-kslzdy8q 92 7 serially serially RB cord-033493-kslzdy8q 92 8 using use VBG cord-033493-kslzdy8q 92 9 the the DT cord-033493-kslzdy8q 92 10 Dulbecco Dulbecco NNP cord-033493-kslzdy8q 92 11 's 's POS cord-033493-kslzdy8q 92 12 modified modify VBN cord-033493-kslzdy8q 92 13 Eagle Eagle NNP cord-033493-kslzdy8q 92 14 's 's POS cord-033493-kslzdy8q 92 15 medium medium NN cord-033493-kslzdy8q 92 16 ( ( -LRB- cord-033493-kslzdy8q 92 17 DMEM DMEM NNP cord-033493-kslzdy8q 92 18 ) ) -RRB- cord-033493-kslzdy8q 92 19 . . . cord-033493-kslzdy8q 93 1 51−56 51−56 CD cord-033493-kslzdy8q 94 1 Then then RB cord-033493-kslzdy8q 94 2 , , , cord-033493-kslzdy8q 94 3 a a DT cord-033493-kslzdy8q 94 4 preparation preparation NN cord-033493-kslzdy8q 94 5 of of IN cord-033493-kslzdy8q 94 6 test test NN cord-033493-kslzdy8q 94 7 compound compound NN cord-033493-kslzdy8q 94 8 stock stock NN cord-033493-kslzdy8q 94 9 solutions solution NNS cord-033493-kslzdy8q 94 10 was be VBD cord-033493-kslzdy8q 94 11 carried carry VBN cord-033493-kslzdy8q 94 12 out out RP cord-033493-kslzdy8q 94 13 in in IN cord-033493-kslzdy8q 94 14 diluted dilute VBN cord-033493-kslzdy8q 94 15 DMSO dmso NN cord-033493-kslzdy8q 94 16 with with IN cord-033493-kslzdy8q 94 17 distilled distil VBN cord-033493-kslzdy8q 94 18 water water NN cord-033493-kslzdy8q 94 19 ( ( -LRB- cord-033493-kslzdy8q 94 20 10 10 CD cord-033493-kslzdy8q 94 21 % % NN cord-033493-kslzdy8q 94 22 ) ) -RRB- cord-033493-kslzdy8q 94 23 . . . cord-033493-kslzdy8q 95 1 Cytotoxicity cytotoxicity NN cord-033493-kslzdy8q 95 2 testing testing NN cord-033493-kslzdy8q 95 3 of of IN cord-033493-kslzdy8q 95 4 the the DT cord-033493-kslzdy8q 95 5 extracts extract NNS cord-033493-kslzdy8q 95 6 was be VBD cord-033493-kslzdy8q 95 7 performed perform VBN cord-033493-kslzdy8q 95 8 with with IN cord-033493-kslzdy8q 95 9 Madin−Darby Madin−Darby NNP cord-033493-kslzdy8q 95 10 canine canine JJ cord-033493-kslzdy8q 95 11 kidney kidney NN cord-033493-kslzdy8q 95 12 ( ( -LRB- cord-033493-kslzdy8q 95 13 MDCK MDCK NNP cord-033493-kslzdy8q 95 14 ) ) -RRB- cord-033493-kslzdy8q 95 15 cells cell NNS cord-033493-kslzdy8q 95 16 using use VBG cord-033493-kslzdy8q 95 17 the the DT cord-033493-kslzdy8q 95 18 method method NN cord-033493-kslzdy8q 95 19 of of IN cord-033493-kslzdy8q 95 20 MTT MTT NNP cord-033493-kslzdy8q 95 21 ( ( -LRB- cord-033493-kslzdy8q 95 22 3-(4,5-dimethylthiazol-2-yl)-2,5diphenyltetrazolium 3-(4,5-dimethylthiazol-2-yl)-2,5diphenyltetrazolium CD cord-033493-kslzdy8q 95 23 bromide bromide NN cord-033493-kslzdy8q 95 24 ) ) -RRB- cord-033493-kslzdy8q 95 25 51 51 CD cord-033493-kslzdy8q 95 26 with with IN cord-033493-kslzdy8q 95 27 some some DT cord-033493-kslzdy8q 95 28 minor minor JJ cord-033493-kslzdy8q 95 29 modifications modification NNS cord-033493-kslzdy8q 95 30 . . . cord-033493-kslzdy8q 96 1 Cells cell NNS cord-033493-kslzdy8q 96 2 were be VBD cord-033493-kslzdy8q 96 3 placed place VBN cord-033493-kslzdy8q 96 4 in in IN cord-033493-kslzdy8q 96 5 96-well 96-well CD cord-033493-kslzdy8q 96 6 plates plate NNS cord-033493-kslzdy8q 96 7 and and CC cord-033493-kslzdy8q 96 8 incubated incubate VBN cord-033493-kslzdy8q 96 9 for for IN cord-033493-kslzdy8q 96 10 1 1 CD cord-033493-kslzdy8q 96 11 day day NN cord-033493-kslzdy8q 96 12 at at IN cord-033493-kslzdy8q 96 13 room room NN cord-033493-kslzdy8q 96 14 temperature temperature NN cord-033493-kslzdy8q 96 15 in in IN cord-033493-kslzdy8q 96 16 5 5 CD cord-033493-kslzdy8q 96 17 % % NN cord-033493-kslzdy8q 96 18 CO co NN cord-033493-kslzdy8q 96 19 2 2 CD cord-033493-kslzdy8q 96 20 . . . cord-033493-kslzdy8q 97 1 After after IN cord-033493-kslzdy8q 97 2 1 1 CD cord-033493-kslzdy8q 97 3 day day NN cord-033493-kslzdy8q 97 4 , , , cord-033493-kslzdy8q 97 5 the the DT cord-033493-kslzdy8q 97 6 cells cell NNS cord-033493-kslzdy8q 97 7 were be VBD cord-033493-kslzdy8q 97 8 treated treat VBN cord-033493-kslzdy8q 97 9 with with IN cord-033493-kslzdy8q 97 10 different different JJ cord-033493-kslzdy8q 97 11 concentrations concentration NNS cord-033493-kslzdy8q 97 12 of of IN cord-033493-kslzdy8q 97 13 the the DT cord-033493-kslzdy8q 97 14 tested test VBN cord-033493-kslzdy8q 97 15 compounds compound NNS cord-033493-kslzdy8q 97 16 . . . cord-033493-kslzdy8q 98 1 The the DT cord-033493-kslzdy8q 98 2 supernatant supernatant NN cord-033493-kslzdy8q 98 3 was be VBD cord-033493-kslzdy8q 98 4 discarded discard VBN cord-033493-kslzdy8q 98 5 after after IN cord-033493-kslzdy8q 98 6 further further JJ cord-033493-kslzdy8q 98 7 24 24 CD cord-033493-kslzdy8q 98 8 h h NN cord-033493-kslzdy8q 98 9 , , , cord-033493-kslzdy8q 98 10 and and CC cord-033493-kslzdy8q 98 11 the the DT cord-033493-kslzdy8q 98 12 cell cell NN cord-033493-kslzdy8q 98 13 monolayers monolayer NNS cord-033493-kslzdy8q 98 14 were be VBD cord-033493-kslzdy8q 98 15 washed wash VBN cord-033493-kslzdy8q 98 16 with with IN cord-033493-kslzdy8q 98 17 a a DT cord-033493-kslzdy8q 98 18 solution solution NN cord-033493-kslzdy8q 98 19 of of IN cord-033493-kslzdy8q 98 20 phosphate phosphate NN cord-033493-kslzdy8q 98 21 saline saline NN cord-033493-kslzdy8q 98 22 ( ( -LRB- cord-033493-kslzdy8q 98 23 PBS PBS NNP cord-033493-kslzdy8q 98 24 ) ) -RRB- cord-033493-kslzdy8q 98 25 . . . cord-033493-kslzdy8q 99 1 An an DT cord-033493-kslzdy8q 99 2 MTT MTT NNP cord-033493-kslzdy8q 99 3 solution solution NN cord-033493-kslzdy8q 99 4 was be VBD cord-033493-kslzdy8q 99 5 added add VBN cord-033493-kslzdy8q 99 6 to to IN cord-033493-kslzdy8q 99 7 each each DT cord-033493-kslzdy8q 99 8 well well RB cord-033493-kslzdy8q 99 9 and and CC cord-033493-kslzdy8q 99 10 incubated incubate VBN cord-033493-kslzdy8q 99 11 at at IN cord-033493-kslzdy8q 99 12 room room NN cord-033493-kslzdy8q 99 13 temperature temperature NN cord-033493-kslzdy8q 99 14 for for IN cord-033493-kslzdy8q 99 15 4 4 CD cord-033493-kslzdy8q 99 16 h h NN cord-033493-kslzdy8q 99 17 , , , cord-033493-kslzdy8q 99 18 and and CC cord-033493-kslzdy8q 99 19 then then RB cord-033493-kslzdy8q 99 20 , , , cord-033493-kslzdy8q 99 21 a a DT cord-033493-kslzdy8q 99 22 medium medium JJ cord-033493-kslzdy8q 99 23 suction suction NN cord-033493-kslzdy8q 99 24 was be VBD cord-033493-kslzdy8q 99 25 applied apply VBN cord-033493-kslzdy8q 99 26 . . . cord-033493-kslzdy8q 100 1 The the DT cord-033493-kslzdy8q 100 2 formazine formazine NN cord-033493-kslzdy8q 100 3 crystals crystal NNS cord-033493-kslzdy8q 100 4 formed form VBN cord-033493-kslzdy8q 100 5 were be VBD cord-033493-kslzdy8q 100 6 then then RB cord-033493-kslzdy8q 100 7 dissolved dissolve VBN cord-033493-kslzdy8q 100 8 in in IN cord-033493-kslzdy8q 100 9 200 200 CD cord-033493-kslzdy8q 100 10 μL μL NNS cord-033493-kslzdy8q 100 11 of of IN cord-033493-kslzdy8q 100 12 acidified acidified JJ cord-033493-kslzdy8q 100 13 isopropanol isopropanol NN cord-033493-kslzdy8q 100 14 . . . cord-033493-kslzdy8q 101 1 The the DT cord-033493-kslzdy8q 101 2 absorbance absorbance NN cord-033493-kslzdy8q 101 3 measurement measurement NN cord-033493-kslzdy8q 101 4 of of IN cord-033493-kslzdy8q 101 5 the the DT cord-033493-kslzdy8q 101 6 formazine formazine NNP cord-033493-kslzdy8q 101 7 solutions solution NNS cord-033493-kslzdy8q 101 8 at at IN cord-033493-kslzdy8q 101 9 λ λ NNP cord-033493-kslzdy8q 101 10 max max NNP cord-033493-kslzdy8q 101 11 of of IN cord-033493-kslzdy8q 101 12 540 540 CD cord-033493-kslzdy8q 101 13 nm nm NN cord-033493-kslzdy8q 101 14 with with IN cord-033493-kslzdy8q 101 15 620 620 CD cord-033493-kslzdy8q 101 16 nm nm NN cord-033493-kslzdy8q 101 17 as as IN cord-033493-kslzdy8q 101 18 the the DT cord-033493-kslzdy8q 101 19 reference reference NN cord-033493-kslzdy8q 101 20 wavelength wavelength NN cord-033493-kslzdy8q 101 21 was be VBD cord-033493-kslzdy8q 101 22 performed perform VBN cord-033493-kslzdy8q 101 23 using use VBG cord-033493-kslzdy8q 101 24 a a DT cord-033493-kslzdy8q 101 25 multiplate multiplate NNP cord-033493-kslzdy8q 101 26 reader reader NN cord-033493-kslzdy8q 101 27 . . . cord-033493-kslzdy8q 102 1 Then then RB cord-033493-kslzdy8q 102 2 , , , cord-033493-kslzdy8q 102 3 the the DT cord-033493-kslzdy8q 102 4 determination determination NN cord-033493-kslzdy8q 102 5 of of IN cord-033493-kslzdy8q 102 6 the the DT cord-033493-kslzdy8q 102 7 cytotoxicity cytotoxicity NN cord-033493-kslzdy8q 102 8 compared compare VBN cord-033493-kslzdy8q 102 9 to to IN cord-033493-kslzdy8q 102 10 the the DT cord-033493-kslzdy8q 102 11 untreated untreated JJ cord-033493-kslzdy8q 102 12 cells cell NNS cord-033493-kslzdy8q 102 13 was be VBD cord-033493-kslzdy8q 102 14 performed perform VBN cord-033493-kslzdy8q 102 15 using use VBG cord-033493-kslzdy8q 102 16 the the DT cord-033493-kslzdy8q 102 17 following follow VBG cord-033493-kslzdy8q 102 18 equation equation NN cord-033493-kslzdy8q 102 19 . . . cord-033493-kslzdy8q 103 1 The the DT cord-033493-kslzdy8q 103 2 plot plot NN cord-033493-kslzdy8q 103 3 of of IN cord-033493-kslzdy8q 103 4 cytotoxicity cytotoxicity NN cord-033493-kslzdy8q 103 5 percentage percentage NN cord-033493-kslzdy8q 103 6 versus versus IN cord-033493-kslzdy8q 103 7 concentration concentration NN cord-033493-kslzdy8q 103 8 of of IN cord-033493-kslzdy8q 103 9 sample sample NN cord-033493-kslzdy8q 103 10 was be VBD cord-033493-kslzdy8q 103 11 used use VBN cord-033493-kslzdy8q 103 12 to to TO cord-033493-kslzdy8q 103 13 calculate calculate VB cord-033493-kslzdy8q 103 14 the the DT cord-033493-kslzdy8q 103 15 concentration concentration NN cord-033493-kslzdy8q 103 16 , , , cord-033493-kslzdy8q 103 17 which which WDT cord-033493-kslzdy8q 103 18 showed show VBD cord-033493-kslzdy8q 103 19 50 50 CD cord-033493-kslzdy8q 103 20 % % NN cord-033493-kslzdy8q 103 21 cytotoxicity cytotoxicity NN cord-033493-kslzdy8q 103 22 ( ( -LRB- cord-033493-kslzdy8q 103 23 LD LD NNP cord-033493-kslzdy8q 103 24 50 50 CD cord-033493-kslzdy8q 103 25 ) ) -RRB- cord-033493-kslzdy8q 103 26 . . . cord-033493-kslzdy8q 104 1 Plaque Plaque NNP cord-033493-kslzdy8q 104 2 Reduction Reduction NNP cord-033493-kslzdy8q 104 3 Assay Assay NNP cord-033493-kslzdy8q 104 4 . . . cord-033493-kslzdy8q 105 1 The the DT cord-033493-kslzdy8q 105 2 plaque plaque NN cord-033493-kslzdy8q 105 3 reduction reduction NN cord-033493-kslzdy8q 105 4 assay assay NN cord-033493-kslzdy8q 105 5 was be VBD cord-033493-kslzdy8q 105 6 performed perform VBN cord-033493-kslzdy8q 105 7 according accord VBG cord-033493-kslzdy8q 105 8 to to IN cord-033493-kslzdy8q 105 9 the the DT cord-033493-kslzdy8q 105 10 method method NN cord-033493-kslzdy8q 105 11 described describe VBN cord-033493-kslzdy8q 105 12 by by IN cord-033493-kslzdy8q 105 13 Hayden Hayden NNP cord-033493-kslzdy8q 105 14 et et NNP cord-033493-kslzdy8q 105 15 al al NNP cord-033493-kslzdy8q 105 16 . . . cord-033493-kslzdy8q 106 1 52 52 CD cord-033493-kslzdy8q 106 2 in in IN cord-033493-kslzdy8q 106 3 a a DT cord-033493-kslzdy8q 106 4 plate plate NN cord-033493-kslzdy8q 106 5 of of IN cord-033493-kslzdy8q 106 6 six six CD cord-033493-kslzdy8q 106 7 wells well NNS cord-033493-kslzdy8q 106 8 in in IN cord-033493-kslzdy8q 106 9 which which WDT cord-033493-kslzdy8q 106 10 the the DT cord-033493-kslzdy8q 106 11 MDCK MDCK NNP cord-033493-kslzdy8q 106 12 cells cell NNS cord-033493-kslzdy8q 106 13 ( ( -LRB- cord-033493-kslzdy8q 106 14 105 105 CD cord-033493-kslzdy8q 106 15 cells/ cells/ CD cord-033493-kslzdy8q 106 16 ml ml NNS cord-033493-kslzdy8q 106 17 ) ) -RRB- cord-033493-kslzdy8q 106 18 were be VBD cord-033493-kslzdy8q 106 19 cultivated cultivate VBN cord-033493-kslzdy8q 106 20 for for IN cord-033493-kslzdy8q 106 21 1 1 CD cord-033493-kslzdy8q 106 22 day day NN cord-033493-kslzdy8q 106 23 at at IN cord-033493-kslzdy8q 106 24 room room NN cord-033493-kslzdy8q 106 25 temperature temperature NN cord-033493-kslzdy8q 106 26 . . . cord-033493-kslzdy8q 107 1 51−56 51−56 CD cord-033493-kslzdy8q 108 1 The the DT cord-033493-kslzdy8q 108 2 virus virus NN cord-033493-kslzdy8q 108 3 A a NN cord-033493-kslzdy8q 108 4 / / SYM cord-033493-kslzdy8q 108 5 CHICKEN/7217B/1/2013 CHICKEN/7217B/1/2013 NNP cord-033493-kslzdy8q 108 6 ( ( -LRB- cord-033493-kslzdy8q 108 7 H5N1 H5N1 NNP cord-033493-kslzdy8q 108 8 ) ) -RRB- cord-033493-kslzdy8q 108 9 was be VBD cord-033493-kslzdy8q 108 10 diluted dilute VBN cord-033493-kslzdy8q 108 11 to to TO cord-033493-kslzdy8q 108 12 give give VB cord-033493-kslzdy8q 108 13 105 105 CD cord-033493-kslzdy8q 108 14 PFU pfu NN cord-033493-kslzdy8q 108 15 / / SYM cord-033493-kslzdy8q 108 16 well well RB cord-033493-kslzdy8q 108 17 and and CC cord-033493-kslzdy8q 108 18 mixed mix VBN cord-033493-kslzdy8q 108 19 with with IN cord-033493-kslzdy8q 108 20 the the DT cord-033493-kslzdy8q 108 21 tested test VBN cord-033493-kslzdy8q 108 22 samples sample NNS cord-033493-kslzdy8q 108 23 and and CC cord-033493-kslzdy8q 108 24 incubated incubate VBN cord-033493-kslzdy8q 108 25 for for IN cord-033493-kslzdy8q 108 26 half half JJ cord-033493-kslzdy8q 108 27 hour hour NN cord-033493-kslzdy8q 108 28 at at IN cord-033493-kslzdy8q 108 29 room room NN cord-033493-kslzdy8q 108 30 temperature temperature NN cord-033493-kslzdy8q 108 31 before before IN cord-033493-kslzdy8q 108 32 being be VBG cord-033493-kslzdy8q 108 33 added add VBN cord-033493-kslzdy8q 108 34 to to IN cord-033493-kslzdy8q 108 35 the the DT cord-033493-kslzdy8q 108 36 cells cell NNS cord-033493-kslzdy8q 108 37 . . . cord-033493-kslzdy8q 109 1 The the DT cord-033493-kslzdy8q 109 2 growth growth NN cord-033493-kslzdy8q 109 3 medium medium NN cord-033493-kslzdy8q 109 4 was be VBD cord-033493-kslzdy8q 109 5 removed remove VBN cord-033493-kslzdy8q 109 6 from from IN cord-033493-kslzdy8q 109 7 the the DT cord-033493-kslzdy8q 109 8 cell cell NN cord-033493-kslzdy8q 109 9 culture culture NN cord-033493-kslzdy8q 109 10 plates plate NNS cord-033493-kslzdy8q 109 11 , , , cord-033493-kslzdy8q 109 12 and and CC cord-033493-kslzdy8q 109 13 mixtures mixture NNS cord-033493-kslzdy8q 109 14 of of IN cord-033493-kslzdy8q 109 15 virus−Cpd virus−cpd NN cord-033493-kslzdy8q 110 1 or or CC cord-033493-kslzdy8q 110 2 virus−extract virus−extract CD cord-033493-kslzdy8q 110 3 and and CC cord-033493-kslzdy8q 110 4 virus−oseltamivir virus−oseltamivir NNP cord-033493-kslzdy8q 110 5 ( ( -LRB- cord-033493-kslzdy8q 110 6 100 100 CD cord-033493-kslzdy8q 110 7 μL μl NN cord-033493-kslzdy8q 110 8 / / SYM cord-033493-kslzdy8q 110 9 well well RB cord-033493-kslzdy8q 110 10 ) ) -RRB- cord-033493-kslzdy8q 110 11 were be VBD cord-033493-kslzdy8q 110 12 inoculated inoculate VBN cord-033493-kslzdy8q 110 13 ( ( -LRB- cord-033493-kslzdy8q 110 14 100 100 CD cord-033493-kslzdy8q 110 15 μL μl NN cord-033493-kslzdy8q 110 16 / / SYM cord-033493-kslzdy8q 110 17 well well RB cord-033493-kslzdy8q 110 18 ) ) -RRB- cord-033493-kslzdy8q 110 19 . . . cord-033493-kslzdy8q 111 1 After after IN cord-033493-kslzdy8q 111 2 1 1 CD cord-033493-kslzdy8q 111 3 hour hour NN cord-033493-kslzdy8q 111 4 of of IN cord-033493-kslzdy8q 111 5 contact contact NN cord-033493-kslzdy8q 111 6 time time NN cord-033493-kslzdy8q 111 7 for for IN cord-033493-kslzdy8q 111 8 viral viral JJ cord-033493-kslzdy8q 111 9 uptake uptake NN cord-033493-kslzdy8q 111 10 , , , cord-033493-kslzdy8q 111 11 3 3 CD cord-033493-kslzdy8q 111 12 mL ml NN cord-033493-kslzdy8q 111 13 of of IN cord-033493-kslzdy8q 111 14 DMEM DMEM NNP cord-033493-kslzdy8q 111 15 was be VBD cord-033493-kslzdy8q 111 16 added add VBN cord-033493-kslzdy8q 111 17 with with IN cord-033493-kslzdy8q 111 18 2 2 CD cord-033493-kslzdy8q 111 19 % % NN cord-033493-kslzdy8q 111 20 agarose agarose JJ cord-033493-kslzdy8q 111 21 on on IN cord-033493-kslzdy8q 111 22 the the DT cord-033493-kslzdy8q 111 23 monolayer monolayer NN cord-033493-kslzdy8q 111 24 cell cell NN cord-033493-kslzdy8q 111 25 , , , cord-033493-kslzdy8q 111 26 and and CC cord-033493-kslzdy8q 111 27 platelets platelet NNS cord-033493-kslzdy8q 111 28 were be VBD cord-033493-kslzdy8q 111 29 left leave VBN cord-033493-kslzdy8q 111 30 to to TO cord-033493-kslzdy8q 111 31 harden harden VB cord-033493-kslzdy8q 111 32 and and CC cord-033493-kslzdy8q 111 33 were be VBD cord-033493-kslzdy8q 111 34 incubated incubate VBN cord-033493-kslzdy8q 111 35 at at IN cord-033493-kslzdy8q 111 36 room room NN cord-033493-kslzdy8q 111 37 temperature temperature NN cord-033493-kslzdy8q 111 38 until until IN cord-033493-kslzdy8q 111 39 viral viral JJ cord-033493-kslzdy8q 111 40 plaques plaque NNS cord-033493-kslzdy8q 111 41 form form NN cord-033493-kslzdy8q 111 42 ( ( -LRB- cord-033493-kslzdy8q 111 43 3−4 3−4 CD cord-033493-kslzdy8q 111 44 days day NNS cord-033493-kslzdy8q 111 45 ) ) -RRB- cord-033493-kslzdy8q 111 46 . . . cord-033493-kslzdy8q 112 1 Formalin Formalin NNP cord-033493-kslzdy8q 112 2 ( ( -LRB- cord-033493-kslzdy8q 112 3 10 10 CD cord-033493-kslzdy8q 112 4 % % NN cord-033493-kslzdy8q 112 5 ) ) -RRB- cord-033493-kslzdy8q 112 6 was be VBD cord-033493-kslzdy8q 112 7 added add VBN cord-033493-kslzdy8q 112 8 for for IN cord-033493-kslzdy8q 112 9 2 2 CD cord-033493-kslzdy8q 112 10 h h NN cord-033493-kslzdy8q 112 11 , , , cord-033493-kslzdy8q 112 12 and and CC cord-033493-kslzdy8q 112 13 then then RB cord-033493-kslzdy8q 112 14 , , , cord-033493-kslzdy8q 112 15 the the DT cord-033493-kslzdy8q 112 16 plates plate NNS cord-033493-kslzdy8q 112 17 were be VBD cord-033493-kslzdy8q 112 18 stained stain VBN cord-033493-kslzdy8q 112 19 with with IN cord-033493-kslzdy8q 112 20 0.1 0.1 CD cord-033493-kslzdy8q 112 21 % % NN cord-033493-kslzdy8q 112 22 crystal crystal NN cord-033493-kslzdy8q 112 23 violet violet NN cord-033493-kslzdy8q 112 24 in in IN cord-033493-kslzdy8q 112 25 H H NNP cord-033493-kslzdy8q 112 26 2 2 CD cord-033493-kslzdy8q 112 27 O. O. NNP cord-033493-kslzdy8q 112 28 Control Control NNP cord-033493-kslzdy8q 112 29 wells well NNS cord-033493-kslzdy8q 112 30 were be VBD cord-033493-kslzdy8q 112 31 included include VBN cord-033493-kslzdy8q 112 32 where where WRB cord-033493-kslzdy8q 112 33 untreated untreated JJ cord-033493-kslzdy8q 112 34 virus virus NN cord-033493-kslzdy8q 112 35 was be VBD cord-033493-kslzdy8q 112 36 incubated incubate VBN cord-033493-kslzdy8q 112 37 with with IN cord-033493-kslzdy8q 112 38 MDCK MDCK NNP cord-033493-kslzdy8q 112 39 cells cell NNS cord-033493-kslzdy8q 112 40 , , , cord-033493-kslzdy8q 112 41 and and CC cord-033493-kslzdy8q 112 42 at at IN cord-033493-kslzdy8q 112 43 the the DT cord-033493-kslzdy8q 112 44 end end NN cord-033493-kslzdy8q 112 45 , , , cord-033493-kslzdy8q 112 46 plaque plaque NN cord-033493-kslzdy8q 112 47 was be VBD cord-033493-kslzdy8q 112 48 counted count VBN cord-033493-kslzdy8q 112 49 and and CC cord-033493-kslzdy8q 112 50 the the DT cord-033493-kslzdy8q 112 51 percentage percentage NN cord-033493-kslzdy8q 112 52 decrease decrease NN cord-033493-kslzdy8q 112 53 in in IN cord-033493-kslzdy8q 112 54 plaque plaque NN cord-033493-kslzdy8q 112 55 formation formation NN cord-033493-kslzdy8q 112 56 compared compare VBN cord-033493-kslzdy8q 112 57 to to TO cord-033493-kslzdy8q 112 58 control control VB cord-033493-kslzdy8q 112 59 wells well NNS cord-033493-kslzdy8q 112 60 was be VBD cord-033493-kslzdy8q 112 61 calculated calculate VBN cord-033493-kslzdy8q 112 62 as as IN cord-033493-kslzdy8q 112 63 follows follow VBZ cord-033493-kslzdy8q 112 64 : : : cord-033493-kslzdy8q 113 1 The the DT cord-033493-kslzdy8q 113 2 Supporting Supporting NNP cord-033493-kslzdy8q 113 3 Information Information NNP cord-033493-kslzdy8q 113 4 is be VBZ cord-033493-kslzdy8q 113 5 available available JJ cord-033493-kslzdy8q 113 6 free free JJ cord-033493-kslzdy8q 113 7 of of IN cord-033493-kslzdy8q 113 8 charge charge NN cord-033493-kslzdy8q 113 9 at at IN cord-033493-kslzdy8q 113 10 https://pubs.acs.org/doi/10.1021/acsomega.0c02675 https://pubs.acs.org/doi/10.1021/acsomega.0c02675 NNP cord-033493-kslzdy8q 113 11 . . . cord-033493-kslzdy8q 114 1 All all DT cord-033493-kslzdy8q 114 2 spectral spectral JJ cord-033493-kslzdy8q 114 3 analysis analysis NN cord-033493-kslzdy8q 114 4 data datum NNS cord-033493-kslzdy8q 114 5 such such JJ cord-033493-kslzdy8q 114 6 as as IN cord-033493-kslzdy8q 114 7 IR IR NNP cord-033493-kslzdy8q 114 8 , , , cord-033493-kslzdy8q 114 9 1 1 CD cord-033493-kslzdy8q 114 10 H h NN cord-033493-kslzdy8q 114 11 NMR nmr NN cord-033493-kslzdy8q 114 12 , , , cord-033493-kslzdy8q 114 13 and and CC cord-033493-kslzdy8q 114 14 13 13 CD cord-033493-kslzdy8q 114 15 C c NN cord-033493-kslzdy8q 114 16 NMR NMR NNP cord-033493-kslzdy8q 114 17 spectra spectra NN cord-033493-kslzdy8q 114 18 for for IN cord-033493-kslzdy8q 114 19 the the DT cord-033493-kslzdy8q 114 20 newly newly RB cord-033493-kslzdy8q 114 21 synthesized synthesize VBN cord-033493-kslzdy8q 114 22 compounds compound NNS cord-033493-kslzdy8q 114 23 ( ( -LRB- cord-033493-kslzdy8q 114 24 PDF PDF NNP cord-033493-kslzdy8q 114 25 ) ) -RRB- cord-033493-kslzdy8q 114 26 Yellow yellow JJ cord-033493-kslzdy8q 114 27 powder powder NN cord-033493-kslzdy8q 114 28 ; ; , cord-033493-kslzdy8q 114 29 ( ( -LRB- cord-033493-kslzdy8q 114 30 ethanol ethanol NN cord-033493-kslzdy8q 114 31 ) ) -RRB- cord-033493-kslzdy8q 114 32 ; ; : cord-033493-kslzdy8q 114 33 yield yield VB cord-033493-kslzdy8q 114 34 53 53 CD cord-033493-kslzdy8q 114 35 % % NN cord-033493-kslzdy8q 114 36 ; ; : cord-033493-kslzdy8q 114 37 mp mp NNP cord-033493-kslzdy8q 114 38 64 64 CD cord-033493-kslzdy8q 114 39 ° ° NN cord-033493-kslzdy8q 114 40 C c NN cord-033493-kslzdy8q 114 41 ; ; : cord-033493-kslzdy8q 114 42 1 1 CD cord-033493-kslzdy8q 114 43 H h NN cord-033493-kslzdy8q 114 44 NMR nmr NN cord-033493-kslzdy8q 114 45 ( ( -LRB- cord-033493-kslzdy8q 114 46 400 400 CD cord-033493-kslzdy8q 114 47 MHz MHz NNPS cord-033493-kslzdy8q 114 48 , , , cord-033493-kslzdy8q 114 49 DMSO DMSO NNP cord-033493-kslzdy8q 114 50 - - HYPH cord-033493-kslzdy8q 114 51 d d NNP cord-033493-kslzdy8q 114 52 6 6 CD cord-033493-kslzdy8q 115 1 ): ): NNP cord-033493-kslzdy8q 116 1 δ δ LS cord-033493-kslzdy8q 116 2 1.36−1.41 1.36−1.41 CD cord-033493-kslzdy8q 117 1 ( ( -LRB- cord-033493-kslzdy8q 117 2 t t NNP cord-033493-kslzdy8q 117 3 , , , cord-033493-kslzdy8q 117 4 3H 3H NNP cord-033493-kslzdy8q 117 5 , , , cord-033493-kslzdy8q 117 6 CH CH NNP cord-033493-kslzdy8q 117 7 3 3 CD cord-033493-kslzdy8q 117 8 ) ) -RRB- cord-033493-kslzdy8q 117 9 , , , cord-033493-kslzdy8q 117 10 2.39 2.39 CD cord-033493-kslzdy8q 117 11 ( ( -LRB- cord-033493-kslzdy8q 117 12 s s NNP cord-033493-kslzdy8q 117 13 , , , cord-033493-kslzdy8q 117 14 3H 3H NNP cord-033493-kslzdy8q 117 15 Method Method NNP cord-033493-kslzdy8q 117 16 : : : cord-033493-kslzdy8q 117 17 hydrazine hydrazine NN cord-033493-kslzdy8q 117 18 hydrate hydrate NN cord-033493-kslzdy8q 117 19 ( ( -LRB- cord-033493-kslzdy8q 117 20 0,50 0,50 NNP cord-033493-kslzdy8q 117 21 g g NN cord-033493-kslzdy8q 117 22 , , , cord-033493-kslzdy8q 117 23 0.01 0.01 CD cord-033493-kslzdy8q 117 24 mol mol NN cord-033493-kslzdy8q 117 25 ) ) -RRB- cord-033493-kslzdy8q 117 26 was be VBD cord-033493-kslzdy8q 117 27 added add VBN cord-033493-kslzdy8q 117 28 to to IN cord-033493-kslzdy8q 117 29 a a DT cord-033493-kslzdy8q 117 30 solution solution NN cord-033493-kslzdy8q 117 31 of of IN cord-033493-kslzdy8q 117 32 ( ( -LRB- cord-033493-kslzdy8q 117 33 E)-ethyl E)-ethyl NNP cord-033493-kslzdy8q 117 34 3-benzamido-2-cyano-3-(methylthio 3-benzamido-2-cyano-3-(methylthio CD cord-033493-kslzdy8q 117 35 ) ) -RRB- cord-033493-kslzdy8q 117 36 acrylate acrylate NN cord-033493-kslzdy8q 117 37 ( ( -LRB- cord-033493-kslzdy8q 117 38 14 14 CD cord-033493-kslzdy8q 117 39 ) ) -RRB- cord-033493-kslzdy8q 117 40 ( ( -LRB- cord-033493-kslzdy8q 117 41 2.90 2.90 CD cord-033493-kslzdy8q 117 42 g g NN cord-033493-kslzdy8q 117 43 , , , cord-033493-kslzdy8q 117 44 0.01 0.01 CD cord-033493-kslzdy8q 117 45 mol mol NN cord-033493-kslzdy8q 117 46 ) ) -RRB- cord-033493-kslzdy8q 117 47 in in IN cord-033493-kslzdy8q 117 48 ethanol ethanol NN cord-033493-kslzdy8q 117 49 ( ( -LRB- cord-033493-kslzdy8q 117 50 20 20 CD cord-033493-kslzdy8q 117 51 mL ml NN cord-033493-kslzdy8q 117 52 ) ) -RRB- cord-033493-kslzdy8q 117 53 in in IN cord-033493-kslzdy8q 117 54 the the DT cord-033493-kslzdy8q 117 55 presence presence NN cord-033493-kslzdy8q 117 56 of of IN cord-033493-kslzdy8q 117 57 drops drop NNS cord-033493-kslzdy8q 117 58 of of IN cord-033493-kslzdy8q 117 59 piperidine piperidine NN cord-033493-kslzdy8q 117 60 . . . cord-033493-kslzdy8q 118 1 The the DT cord-033493-kslzdy8q 118 2 mixture mixture NN cord-033493-kslzdy8q 118 3 was be VBD cord-033493-kslzdy8q 118 4 heated heat VBN cord-033493-kslzdy8q 118 5 under under IN cord-033493-kslzdy8q 118 6 reflux reflux NN cord-033493-kslzdy8q 118 7 for for IN cord-033493-kslzdy8q 118 8 2 2 CD cord-033493-kslzdy8q 118 9 h h NN cord-033493-kslzdy8q 118 10 and and CC cord-033493-kslzdy8q 118 11 then then RB cord-033493-kslzdy8q 118 12 poured pour VBD cord-033493-kslzdy8q 118 13 onto onto IN cord-033493-kslzdy8q 118 14 ice ice NN cord-033493-kslzdy8q 118 15 . . . cord-033493-kslzdy8q 119 1 The the DT cord-033493-kslzdy8q 119 2 solid solid JJ cord-033493-kslzdy8q 119 3 product product NN cord-033493-kslzdy8q 119 4 was be VBD cord-033493-kslzdy8q 119 5 filtered filter VBN cord-033493-kslzdy8q 119 6 off off RP cord-033493-kslzdy8q 119 7 , , , cord-033493-kslzdy8q 119 8 dried dry VBN cord-033493-kslzdy8q 119 9 Synthesis Synthesis NNP cord-033493-kslzdy8q 119 10 of of IN cord-033493-kslzdy8q 119 11 acyclic acyclic NNP cord-033493-kslzdy8q 119 12 thioglucosides thioglucoside NNS cord-033493-kslzdy8q 119 13 21a 21a NNS cord-033493-kslzdy8q 119 14 , , , cord-033493-kslzdy8q 120 1 b. b. NNP cord-033493-kslzdy8q 121 1 Method method NN cord-033493-kslzdy8q 121 2 : : : cord-033493-kslzdy8q 121 3 a a DT cord-033493-kslzdy8q 121 4 mixture mixture NN cord-033493-kslzdy8q 121 5 of of IN cord-033493-kslzdy8q 121 6 malononitrile malononitrile NN cord-033493-kslzdy8q 121 7 ( ( -LRB- cord-033493-kslzdy8q 121 8 0.66 0.66 CD cord-033493-kslzdy8q 121 9 g g NN cord-033493-kslzdy8q 121 10 , , , cord-033493-kslzdy8q 121 11 0.01 0.01 CD cord-033493-kslzdy8q 121 12 mol mol NN cord-033493-kslzdy8q 121 13 ) ) -RRB- cord-033493-kslzdy8q 121 14 or or CC cord-033493-kslzdy8q 121 15 ethyl ethyl NNP cord-033493-kslzdy8q 121 16 cyanoacetate cyanoacetate NN cord-033493-kslzdy8q 121 17 ( ( -LRB- cord-033493-kslzdy8q 121 18 1.13 1.13 CD cord-033493-kslzdy8q 121 19 g g NN cord-033493-kslzdy8q 121 20 , , , cord-033493-kslzdy8q 121 21 0.01 0.01 CD cord-033493-kslzdy8q 121 22 mol mol NN cord-033493-kslzdy8q 121 23 ) ) -RRB- cord-033493-kslzdy8q 121 24 and and CC cord-033493-kslzdy8q 121 25 benzoyl benzoyl NN cord-033493-kslzdy8q 121 26 isothiocyanate isothiocyanate NN cord-033493-kslzdy8q 121 27 ( ( -LRB- cord-033493-kslzdy8q 121 28 1.63 1.63 CD cord-033493-kslzdy8q 121 29 g g NN cord-033493-kslzdy8q 121 30 , , , cord-033493-kslzdy8q 121 31 0.01 0.01 CD cord-033493-kslzdy8q 121 32 mol mol NN cord-033493-kslzdy8q 121 33 ) ) -RRB- cord-033493-kslzdy8q 121 34 was be VBD cord-033493-kslzdy8q 121 35 heated heat VBN cord-033493-kslzdy8q 121 36 for for IN cord-033493-kslzdy8q 121 37 10−20 10−20 CD cord-033493-kslzdy8q 121 38 min min NN cord-033493-kslzdy8q 121 39 in in IN cord-033493-kslzdy8q 121 40 ethanol ethanol NN cord-033493-kslzdy8q 121 41 11 11 CD cord-033493-kslzdy8q 121 42 g g NN cord-033493-kslzdy8q 121 43 , , , cord-033493-kslzdy8q 121 44 0.01 0.01 CD cord-033493-kslzdy8q 121 45 mol mol NN cord-033493-kslzdy8q 121 46 ) ) -RRB- cord-033493-kslzdy8q 121 47 was be VBD cord-033493-kslzdy8q 121 48 added add VBN cord-033493-kslzdy8q 121 49 . . . cord-033493-kslzdy8q 122 1 The the DT cord-033493-kslzdy8q 122 2 reaction reaction NN cord-033493-kslzdy8q 122 3 mixture mixture NN cord-033493-kslzdy8q 122 4 was be VBD cord-033493-kslzdy8q 122 5 stirred stir VBN cord-033493-kslzdy8q 122 6 overnight overnight RB cord-033493-kslzdy8q 122 7 at at IN cord-033493-kslzdy8q 122 8 room room NN cord-033493-kslzdy8q 122 9 temperature temperature NN cord-033493-kslzdy8q 122 10 . . . cord-033493-kslzdy8q 123 1 The the DT cord-033493-kslzdy8q 123 2 resulting result VBG cord-033493-kslzdy8q 123 3 solid solid NN cord-033493-kslzdy8q 123 4 was be VBD cord-033493-kslzdy8q 123 5 collected collect VBN cord-033493-kslzdy8q 123 6 by by IN cord-033493-kslzdy8q 123 7 filtration filtration NN cord-033493-kslzdy8q 123 8 and and CC cord-033493-kslzdy8q 123 9 was be VBD cord-033493-kslzdy8q 123 10 separated separate VBN cord-033493-kslzdy8q 123 11 from from IN cord-033493-kslzdy8q 123 12 traces trace NNS cord-033493-kslzdy8q 123 13 of of IN cord-033493-kslzdy8q 123 14 the the DT cord-033493-kslzdy8q 123 15 reactant reactant NN cord-033493-kslzdy8q 123 16 by by IN cord-033493-kslzdy8q 123 17 preparative preparative JJ cord-033493-kslzdy8q 123 18 thinlayer thinlayer NN cord-033493-kslzdy8q 123 19 chromatography chromatography NN cord-033493-kslzdy8q 123 20 using use VBG cord-033493-kslzdy8q 123 21 DCM DCM NNP cord-033493-kslzdy8q 123 22 as as IN cord-033493-kslzdy8q 123 23 an an DT cord-033493-kslzdy8q 123 24 eluent eluent NN cord-033493-kslzdy8q 123 25 where where WRB cord-033493-kslzdy8q 123 26 compounds compound NNS cord-033493-kslzdy8q 123 27 21a 21a VBP cord-033493-kslzdy8q 123 28 Yellow yellow JJ cord-033493-kslzdy8q 123 29 powder powder NN cord-033493-kslzdy8q 123 30 ; ; : cord-033493-kslzdy8q 123 31 yield yield VBP cord-033493-kslzdy8q 123 32 84 84 CD cord-033493-kslzdy8q 123 33 % % NN cord-033493-kslzdy8q 123 34 ; ; , cord-033493-kslzdy8q 123 35 mp>300 mp>300 JJ cord-033493-kslzdy8q 123 36 ° ° NN cord-033493-kslzdy8q 123 37 C c NN cord-033493-kslzdy8q 123 38 ; ; : cord-033493-kslzdy8q 123 39 1 1 CD cord-033493-kslzdy8q 123 40 H h NN cord-033493-kslzdy8q 123 41 NMR nmr NN cord-033493-kslzdy8q 123 42 ( ( -LRB- cord-033493-kslzdy8q 123 43 400 400 CD cord-033493-kslzdy8q 123 44 MHz MHz NNPS cord-033493-kslzdy8q 123 45 , , . cord-033493-kslzdy8q 124 1 DMSO DMSO NNP cord-033493-kslzdy8q 124 2 - - HYPH cord-033493-kslzdy8q 124 3 d d NNP cord-033493-kslzdy8q 124 4 6 6 CD cord-033493-kslzdy8q 124 5 ): ): NN cord-033493-kslzdy8q 125 1 δ δ LS cord-033493-kslzdy8q 125 2 1.18−1.27 1.18−1.27 CD cord-033493-kslzdy8q 126 1 ( ( -LRB- cord-033493-kslzdy8q 126 2 t t NNP cord-033493-kslzdy8q 126 3 , , , cord-033493-kslzdy8q 126 4 3H 3H NNP cord-033493-kslzdy8q 126 5 , , , cord-033493-kslzdy8q 126 6 CH2-CH CH2-CH NNP cord-033493-kslzdy8q 126 7 3 3 CD cord-033493-kslzdy8q 126 8 ) ) -RRB- cord-033493-kslzdy8q 126 9 , , , cord-033493-kslzdy8q 126 10 1.59−2.00 1.59−2.00 CD cord-033493-kslzdy8q 126 11 ( ( -LRB- cord-033493-kslzdy8q 126 12 4 4 CD cord-033493-kslzdy8q 126 13 s s NN cord-033493-kslzdy8q 126 14 , , , cord-033493-kslzdy8q 126 15 12H 12H NNP cord-033493-kslzdy8q 126 16 Synthesis Synthesis NNP cord-033493-kslzdy8q 126 17 of of IN cord-033493-kslzdy8q 126 18 new new JJ cord-033493-kslzdy8q 126 19 pyrazole pyrazole NN cord-033493-kslzdy8q 126 20 derivatives derivative NNS cord-033493-kslzdy8q 126 21 and and CC cord-033493-kslzdy8q 126 22 their -PRON- PRP$ cord-033493-kslzdy8q 126 23 anticancer anticancer JJ cord-033493-kslzdy8q 126 24 evaluation evaluation NN cord-033493-kslzdy8q 126 25 Antimicrobial Antimicrobial NNP cord-033493-kslzdy8q 126 26 screening screening NN cord-033493-kslzdy8q 126 27 and and CC cord-033493-kslzdy8q 126 28 one one CD cord-033493-kslzdy8q 126 29 - - HYPH cord-033493-kslzdy8q 126 30 pot pot NN cord-033493-kslzdy8q 126 31 synthesis synthesis NN cord-033493-kslzdy8q 126 32 of of IN cord-033493-kslzdy8q 126 33 4-(substituted 4-(substituted CD cord-033493-kslzdy8q 126 34 - - HYPH cord-033493-kslzdy8q 126 35 anilinomethyl)-3-(2-naphthyl)-1-phenyl-1H anilinomethyl)-3-(2-naphthyl)-1-phenyl-1H NNP cord-033493-kslzdy8q 126 36 - - HYPH cord-033493-kslzdy8q 126 37 pyrazole pyrazole NN cord-033493-kslzdy8q 126 38 derivatives derivative NNS cord-033493-kslzdy8q 126 39 Fused fuse VBN cord-033493-kslzdy8q 126 40 pyrazole pyrazole NN cord-033493-kslzdy8q 126 41 derivatives derivative NNS cord-033493-kslzdy8q 126 42 as as IN cord-033493-kslzdy8q 126 43 kinase kinase NN cord-033493-kslzdy8q 126 44 inhibitors inhibitor NNS cord-033493-kslzdy8q 126 45 , , , cord-033493-kslzdy8q 126 46 WO WO MD cord-033493-kslzdy8q 126 47 Patent patent NN cord-033493-kslzdy8q 126 48 Novel Novel NNP cord-033493-kslzdy8q 126 49 Synthesis Synthesis NNP cord-033493-kslzdy8q 126 50 and and CC cord-033493-kslzdy8q 126 51 Biological Biological NNP cord-033493-kslzdy8q 126 52 Evaluation Evaluation NNP cord-033493-kslzdy8q 126 53 of of IN cord-033493-kslzdy8q 126 54 the the DT cord-033493-kslzdy8q 126 55 First First NNP cord-033493-kslzdy8q 126 56 Pyrazole Pyrazole NNP cord-033493-kslzdy8q 126 57 Thioglycosides Thioglycosides NNP cord-033493-kslzdy8q 126 58 as as IN cord-033493-kslzdy8q 126 59 Pyrazofurin Pyrazofurin NNP cord-033493-kslzdy8q 126 60 Analogues Analogues NNP cord-033493-kslzdy8q 126 61 Novel Novel NNP cord-033493-kslzdy8q 126 62 synthesis synthesis NN cord-033493-kslzdy8q 126 63 of of IN cord-033493-kslzdy8q 126 64 new new JJ cord-033493-kslzdy8q 126 65 pyrazole pyrazole NNP cord-033493-kslzdy8q 126 66 thioglycosides thioglycosides NNP cord-033493-kslzdy8q 126 67 as as IN cord-033493-kslzdy8q 126 68 pyrazomycin pyrazomycin NNP cord-033493-kslzdy8q 126 69 analogues analogue NNS cord-033493-kslzdy8q 126 70 pyrimidine pyrimidine NN cord-033493-kslzdy8q 126 71 TTK TTK NNP cord-033493-kslzdy8q 126 72 Inhibitors Inhibitors NNPS cord-033493-kslzdy8q 126 73 : : : cord-033493-kslzdy8q 126 74 CFI-402257 CFI-402257 NNP cord-033493-kslzdy8q 126 75 is be VBZ cord-033493-kslzdy8q 126 76 a a DT cord-033493-kslzdy8q 126 77 Potent potent JJ cord-033493-kslzdy8q 126 78 , , , cord-033493-kslzdy8q 126 79 Selective selective JJ cord-033493-kslzdy8q 126 80 , , , cord-033493-kslzdy8q 126 81 Bioavailable Bioavailable NNP cord-033493-kslzdy8q 126 82 Anticancer Anticancer NNP cord-033493-kslzdy8q 126 83 Agent Agent NNP cord-033493-kslzdy8q 126 84 Design Design NNP cord-033493-kslzdy8q 126 85 and and CC cord-033493-kslzdy8q 126 86 synthesis synthesis NN cord-033493-kslzdy8q 126 87 of of IN cord-033493-kslzdy8q 126 88 novel novel JJ cord-033493-kslzdy8q 126 89 pyrazolo[1,5-a]pyrimidine pyrazolo[1,5-a]pyrimidine JJ cord-033493-kslzdy8q 126 90 derivatives derivative NNS cord-033493-kslzdy8q 126 91 bearing bear VBG cord-033493-kslzdy8q 126 92 nitrogen nitrogen NN cord-033493-kslzdy8q 126 93 mustard mustard NN cord-033493-kslzdy8q 126 94 moiety moiety NN cord-033493-kslzdy8q 126 95 and and CC cord-033493-kslzdy8q 126 96 evaluation evaluation NN cord-033493-kslzdy8q 126 97 of of IN cord-033493-kslzdy8q 126 98 their -PRON- PRP$ cord-033493-kslzdy8q 126 99 antitumor antitumor JJ cord-033493-kslzdy8q 126 100 activity activity NN cord-033493-kslzdy8q 126 101 in in IN cord-033493-kslzdy8q 126 102 vitro vitro FW cord-033493-kslzdy8q 126 103 and and CC cord-033493-kslzdy8q 126 104 in in IN cord-033493-kslzdy8q 126 105 vivo vivo NNP cord-033493-kslzdy8q 126 106 Regioselective Regioselective NNP cord-033493-kslzdy8q 126 107 synthesis synthesis NN cord-033493-kslzdy8q 126 108 of of IN cord-033493-kslzdy8q 126 109 1-and 1-and CD cord-033493-kslzdy8q 126 110 4-substituted 4-substituted CD cord-033493-kslzdy8q 126 111 7-oxopyrazolo[1,5-a]pyrimidine-3-carboxamides 7-oxopyrazolo[1,5-a]pyrimidine-3-carboxamides CD cord-033493-kslzdy8q 126 112 , , , cord-033493-kslzdy8q 126 113 5-a]pyrimidine 5-a]pyrimidine CD cord-033493-kslzdy8q 126 114 - - HYPH cord-033493-kslzdy8q 126 115 based base VBN cord-033493-kslzdy8q 126 116 inhibitors inhibitor NNS cord-033493-kslzdy8q 126 117 of of IN cord-033493-kslzdy8q 126 118 HCV HCV NNP cord-033493-kslzdy8q 126 119 polymerase polymerase NN cord-033493-kslzdy8q 126 120 Discovery Discovery NNP cord-033493-kslzdy8q 126 121 of of IN cord-033493-kslzdy8q 126 122 Novel Novel NNP cord-033493-kslzdy8q 126 123 2-Anilinopyrazolo[1,5-a]pyrimidine 2-anilinopyrazolo[1,5-a]pyrimidine CD cord-033493-kslzdy8q 126 124 Derivatives Derivatives NNPS cord-033493-kslzdy8q 126 125 as as IN cord-033493-kslzdy8q 126 126 c c NNP cord-033493-kslzdy8q 126 127 - - HYPH cord-033493-kslzdy8q 126 128 Src Src NNP cord-033493-kslzdy8q 126 129 Kinase Kinase NNP cord-033493-kslzdy8q 126 130 Inhibitors Inhibitors NNP cord-033493-kslzdy8q 126 131 for for IN cord-033493-kslzdy8q 126 132 the the DT cord-033493-kslzdy8q 126 133 Treatment Treatment NNP cord-033493-kslzdy8q 126 134 of of IN cord-033493-kslzdy8q 126 135 Acute Acute NNP cord-033493-kslzdy8q 126 136 Ischemic Ischemic NNP cord-033493-kslzdy8q 126 137 Stroke Stroke NNP cord-033493-kslzdy8q 126 138 Reactions reaction NNS cord-033493-kslzdy8q 126 139 with with IN cord-033493-kslzdy8q 126 140 3,5-Diaminopyrazoles 3,5-diaminopyrazoles CD cord-033493-kslzdy8q 126 141 : : : cord-033493-kslzdy8q 126 142 New new JJ cord-033493-kslzdy8q 126 143 Routes route NNS cord-033493-kslzdy8q 126 144 to to IN cord-033493-kslzdy8q 126 145 Pyrazolo[1,5-α]pyrimidines Pyrazolo[1,5-α]pyrimidines NNPS cord-033493-kslzdy8q 126 146 Novel Novel NNP cord-033493-kslzdy8q 126 147 synthesis synthesis NN cord-033493-kslzdy8q 126 148 of of IN cord-033493-kslzdy8q 126 149 mercaptopurine mercaptopurine NNP cord-033493-kslzdy8q 126 150 and and CC cord-033493-kslzdy8q 126 151 pentaaza pentaaza NNP cord-033493-kslzdy8q 126 152 - - HYPH cord-033493-kslzdy8q 126 153 as as IN cord-033493-kslzdy8q 126 154 - - HYPH cord-033493-kslzdy8q 126 155 indacene indacene NNP cord-033493-kslzdy8q 127 1 analogues analogue NNS cord-033493-kslzdy8q 127 2 : : : cord-033493-kslzdy8q 127 3 Reaction reaction NN cord-033493-kslzdy8q 127 4 of of IN cord-033493-kslzdy8q 127 5 [ [ -LRB- cord-033493-kslzdy8q 127 6 bis(methylthio)methylene]malononitrile bis(methylthio)methylene]malononitrile CD cord-033493-kslzdy8q 127 7 and and CC cord-033493-kslzdy8q 127 8 ethyl-2-cyano-3,3-bis(methylthio)acrylate ethyl-2-cyano-3,3-bis(methylthio)acrylate XX cord-033493-kslzdy8q 127 9 with with IN cord-033493-kslzdy8q 127 10 5-aminopyrazoles 5-aminopyrazoles CD cord-033493-kslzdy8q 127 11 Design Design NNP cord-033493-kslzdy8q 127 12 , , , cord-033493-kslzdy8q 127 13 synthesis synthesis NN cord-033493-kslzdy8q 127 14 , , , cord-033493-kslzdy8q 127 15 docking docking NN cord-033493-kslzdy8q 127 16 , , , cord-033493-kslzdy8q 127 17 and and CC cord-033493-kslzdy8q 127 18 antimicrobial antimicrobial JJ cord-033493-kslzdy8q 127 19 evaluation evaluation NN cord-033493-kslzdy8q 127 20 of of IN cord-033493-kslzdy8q 127 21 some some DT cord-033493-kslzdy8q 127 22 novel novel JJ cord-033493-kslzdy8q 127 23 pyrazolo[1,5-a pyrazolo[1,5-a NN cord-033493-kslzdy8q 127 24 ] ] -RRB- cord-033493-kslzdy8q 127 25 pyrimidines pyrimidine NNS cord-033493-kslzdy8q 127 26 and and CC cord-033493-kslzdy8q 127 27 their -PRON- PRP$ cord-033493-kslzdy8q 127 28 corresponding correspond VBG cord-033493-kslzdy8q 127 29 cycloalkane cycloalkane NN cord-033493-kslzdy8q 127 30 ring ring NN cord-033493-kslzdy8q 127 31 - - HYPH cord-033493-kslzdy8q 127 32 fused fuse VBN cord-033493-kslzdy8q 127 33 derivatives derivative NNS cord-033493-kslzdy8q 127 34 as as IN cord-033493-kslzdy8q 127 35 purine purine NNP cord-033493-kslzdy8q 127 36 analogs analogs NNP cord-033493-kslzdy8q 128 1 Potential potential JJ cord-033493-kslzdy8q 128 2 purine purine NN cord-033493-kslzdy8q 128 3 analogue analogue NN cord-033493-kslzdy8q 128 4 antagonists antagonist NNS cord-033493-kslzdy8q 128 5 : : : cord-033493-kslzdy8q 128 6 Synthesis synthesis NN cord-033493-kslzdy8q 128 7 of of IN cord-033493-kslzdy8q 128 8 novel novel JJ cord-033493-kslzdy8q 128 9 cycloalkane cycloalkane NN cord-033493-kslzdy8q 128 10 ring ring NN cord-033493-kslzdy8q 128 11 - - HYPH cord-033493-kslzdy8q 128 12 fused fuse VBN cord-033493-kslzdy8q 128 13 pyrazolo[1,5-a]pyrimidines pyrazolo[1,5-a]pyrimidines NNPS cord-033493-kslzdy8q 128 14 1,3,5-Triazine 1,3,5-triazine NN cord-033493-kslzdy8q 128 15 - - HYPH cord-033493-kslzdy8q 128 16 based base VBN cord-033493-kslzdy8q 128 17 analogues analogue NNS cord-033493-kslzdy8q 128 18 of of IN cord-033493-kslzdy8q 128 19 purine purine NN cord-033493-kslzdy8q 128 20 : : : cord-033493-kslzdy8q 129 1 From from IN cord-033493-kslzdy8q 129 2 isosteres isostere NNS cord-033493-kslzdy8q 129 3 to to IN cord-033493-kslzdy8q 129 4 privileged privileged JJ cord-033493-kslzdy8q 129 5 scaffolds scaffold NNS cord-033493-kslzdy8q 129 6 in in IN cord-033493-kslzdy8q 129 7 medicinal medicinal JJ cord-033493-kslzdy8q 129 8 chemistry chemistry NN cord-033493-kslzdy8q 129 9 Synthesis Synthesis NNP cord-033493-kslzdy8q 129 10 and and CC cord-033493-kslzdy8q 129 11 biological biological JJ cord-033493-kslzdy8q 129 12 activity activity NN cord-033493-kslzdy8q 129 13 yl)benzamides yl)benzamide NNS cord-033493-kslzdy8q 129 14 as as IN cord-033493-kslzdy8q 129 15 novel novel NN cord-033493-kslzdy8q 129 16 , , , cord-033493-kslzdy8q 129 17 highly highly RB cord-033493-kslzdy8q 129 18 potent potent JJ cord-033493-kslzdy8q 129 19 and and CC cord-033493-kslzdy8q 129 20 selective selective JJ cord-033493-kslzdy8q 129 21 , , , cord-033493-kslzdy8q 129 22 orally orally RB cord-033493-kslzdy8q 129 23 bioavailable bioavailable JJ cord-033493-kslzdy8q 129 24 inhibitors inhibitor NNS cord-033493-kslzdy8q 129 25 of of IN cord-033493-kslzdy8q 129 26 Tyrosine Tyrosine NNP cord-033493-kslzdy8q 129 27 Threonine Threonine NNP cord-033493-kslzdy8q 129 28 Kinase Kinase NNP cord-033493-kslzdy8q 129 29 TTK TTK NNP cord-033493-kslzdy8q 129 30 Reactions reaction NNS cord-033493-kslzdy8q 129 31 of of IN cord-033493-kslzdy8q 129 32 chlorocarbonyl chlorocarbonyl NN cord-033493-kslzdy8q 129 33 isocyanate isocyanate NN cord-033493-kslzdy8q 129 34 with with IN cord-033493-kslzdy8q 129 35 5-aminopyrazoles 5-aminopyrazoles CD cord-033493-kslzdy8q 129 36 and and CC cord-033493-kslzdy8q 129 37 active active JJ cord-033493-kslzdy8q 129 38 methylene methylene NN cord-033493-kslzdy8q 129 39 nitriles nitrile NNS cord-033493-kslzdy8q 129 40 : : : cord-033493-kslzdy8q 129 41 A a DT cord-033493-kslzdy8q 129 42 novel novel JJ cord-033493-kslzdy8q 129 43 synthesis synthesis NN cord-033493-kslzdy8q 129 44 of of IN cord-033493-kslzdy8q 129 45 pyrazolo[1,5-a]-1,3,5-triazines pyrazolo[1,5-a]-1,3,5-triazines NNPS cord-033493-kslzdy8q 129 46 and and CC cord-033493-kslzdy8q 129 47 barbiturates barbiturate NNS cord-033493-kslzdy8q 130 1 The the DT cord-033493-kslzdy8q 130 2 reaction reaction NN cord-033493-kslzdy8q 130 3 of of IN cord-033493-kslzdy8q 130 4 dimethyl dimethyl NN cord-033493-kslzdy8q 130 5 Ncyanodithioiminocarbonate Ncyanodithioiminocarbonate NNP cord-033493-kslzdy8q 130 6 with with IN cord-033493-kslzdy8q 130 7 amino amino NN cord-033493-kslzdy8q 130 8 - - : cord-033493-kslzdy8q 130 9 and and CC cord-033493-kslzdy8q 130 10 oxo oxo NN cord-033493-kslzdy8q 130 11 - - HYPH cord-033493-kslzdy8q 130 12 azoles azole NNS cord-033493-kslzdy8q 130 13 : : : cord-033493-kslzdy8q 130 14 a a DT cord-033493-kslzdy8q 130 15 new new JJ cord-033493-kslzdy8q 130 16 general general JJ cord-033493-kslzdy8q 130 17 synthesis synthesis NN cord-033493-kslzdy8q 130 18 of of IN cord-033493-kslzdy8q 130 19 methylsulfanylazoloazines methylsulfanylazoloazine NNS cord-033493-kslzdy8q 130 20 5-amino-3-anilino 5-amino-3-anilino NNP cord-033493-kslzdy8q 130 21 - - HYPH cord-033493-kslzdy8q 130 22 N-(chlorophenyl)-1H n-(chlorophenyl)-1h NN cord-033493-kslzdy8q 130 23 - - HYPH cord-033493-kslzdy8q 130 24 pyrazole-4-carboxamide pyrazole-4-carboxamide JJ cord-033493-kslzdy8q 130 25 ethanol ethanol NN cord-033493-kslzdy8q 130 26 solvate solvate NN cord-033493-kslzdy8q 130 27 Novel novel JJ cord-033493-kslzdy8q 130 28 synthesis synthesis NN cord-033493-kslzdy8q 130 29 of of IN cord-033493-kslzdy8q 130 30 fluorinated fluorinate VBN cord-033493-kslzdy8q 130 31 cyanoketene cyanoketene NNP cord-033493-kslzdy8q 130 32 N N NNP cord-033493-kslzdy8q 130 33 , , , cord-033493-kslzdy8q 130 34 S S NNP cord-033493-kslzdy8q 130 35 - - HYPH cord-033493-kslzdy8q 130 36 acetals acetal NNS cord-033493-kslzdy8q 130 37 and and CC cord-033493-kslzdy8q 130 38 their -PRON- PRP$ cord-033493-kslzdy8q 130 39 conversions conversion NNS cord-033493-kslzdy8q 130 40 to to IN cord-033493-kslzdy8q 130 41 fluorinated fluorinate VBN cord-033493-kslzdy8q 130 42 pyrazole pyrazole NN cord-033493-kslzdy8q 130 43 derivatives derivative NNS cord-033493-kslzdy8q 130 44 . . . cord-033493-kslzdy8q 131 1 Phosphor Phosphor NNP cord-033493-kslzdy8q 131 2 . . . cord-033493-kslzdy8q 132 1 Sulfur Sulfur NNP cord-033493-kslzdy8q 132 2 Silicon Silicon NNP cord-033493-kslzdy8q 132 3 Relat Relat NNP cord-033493-kslzdy8q 132 4 Novel Novel NNP cord-033493-kslzdy8q 132 5 cyanoketene cyanoketene NNP cord-033493-kslzdy8q 132 6 N N NNP cord-033493-kslzdy8q 132 7 , , , cord-033493-kslzdy8q 132 8 S S NNP cord-033493-kslzdy8q 132 9 - - HYPH cord-033493-kslzdy8q 132 10 acetals acetal NNS cord-033493-kslzdy8q 132 11 and and CC cord-033493-kslzdy8q 132 12 pyrazole pyrazole NN cord-033493-kslzdy8q 132 13 derivatives derivative NNS cord-033493-kslzdy8q 132 14 using use VBG cord-033493-kslzdy8q 132 15 potassium potassium NN cord-033493-kslzdy8q 132 16 2-cyanoethylene-1-thiolates 2-cyanoethylene-1-thiolates CD cord-033493-kslzdy8q 132 17 Direct direct JJ cord-033493-kslzdy8q 132 18 route route NN cord-033493-kslzdy8q 132 19 to to IN cord-033493-kslzdy8q 132 20 a a DT cord-033493-kslzdy8q 132 21 new new JJ cord-033493-kslzdy8q 132 22 class class NN cord-033493-kslzdy8q 132 23 of of IN cord-033493-kslzdy8q 132 24 acrylamide acrylamide NN cord-033493-kslzdy8q 132 25 thioglycosides thioglycoside NNS cord-033493-kslzdy8q 132 26 and and CC cord-033493-kslzdy8q 132 27 their -PRON- PRP$ cord-033493-kslzdy8q 132 28 conversions conversion NNS cord-033493-kslzdy8q 132 29 to to IN cord-033493-kslzdy8q 132 30 pyrazole pyrazole NNP cord-033493-kslzdy8q 132 31 derivatives derivative NNS cord-033493-kslzdy8q 132 32 Synthesis Synthesis NNP cord-033493-kslzdy8q 132 33 of of IN cord-033493-kslzdy8q 132 34 some some DT cord-033493-kslzdy8q 132 35 novel novel NN cord-033493-kslzdy8q 132 36 α α NN cord-033493-kslzdy8q 132 37 - - HYPH cord-033493-kslzdy8q 132 38 cyanoketene cyanoketene NNP cord-033493-kslzdy8q 132 39 S S NNP cord-033493-kslzdy8q 132 40 , , , cord-033493-kslzdy8q 132 41 S S NNP cord-033493-kslzdy8q 132 42 - - HYPH cord-033493-kslzdy8q 132 43 acetals acetal NNS cord-033493-kslzdy8q 132 44 and and CC cord-033493-kslzdy8q 132 45 their -PRON- PRP$ cord-033493-kslzdy8q 132 46 use use NN cord-033493-kslzdy8q 132 47 in in IN cord-033493-kslzdy8q 132 48 heterocyclic heterocyclic JJ cord-033493-kslzdy8q 132 49 synthesis synthesis NN cord-033493-kslzdy8q 133 1 Potassium potassium NN cord-033493-kslzdy8q 133 2 2-cyanoethylene-1-thiolate 2-cyanoethylene-1-thiolate CD cord-033493-kslzdy8q 133 3 derivatives derivative NNS cord-033493-kslzdy8q 133 4 : : : cord-033493-kslzdy8q 133 5 A a DT cord-033493-kslzdy8q 133 6 new new JJ cord-033493-kslzdy8q 133 7 preparative preparative JJ cord-033493-kslzdy8q 133 8 route route NN cord-033493-kslzdy8q 133 9 to to IN cord-033493-kslzdy8q 133 10 2-cyanoketene 2-cyanoketene NNP cord-033493-kslzdy8q 133 11 S S NNP cord-033493-kslzdy8q 133 12 , , , cord-033493-kslzdy8q 133 13 N N NNP cord-033493-kslzdy8q 133 14 - - HYPH cord-033493-kslzdy8q 133 15 acetals acetal NNS cord-033493-kslzdy8q 133 16 and and CC cord-033493-kslzdy8q 133 17 pyrazole pyrazole NNP cord-033493-kslzdy8q 133 18 derivatives derivative NNS cord-033493-kslzdy8q 133 19 Synthesis Synthesis NNP cord-033493-kslzdy8q 133 20 of of IN cord-033493-kslzdy8q 133 21 some some DT cord-033493-kslzdy8q 133 22 Pyrazolopyrimidines Pyrazolopyrimidines NNPS cord-033493-kslzdy8q 133 23 as as IN cord-033493-kslzdy8q 133 24 Purine Purine NNP cord-033493-kslzdy8q 133 25 Analogues Analogues NNP cord-033493-kslzdy8q 133 26 Synthesis Synthesis NNP cord-033493-kslzdy8q 133 27 and and CC cord-033493-kslzdy8q 133 28 anti anti JJ cord-033493-kslzdy8q 133 29 - - JJ cord-033493-kslzdy8q 133 30 tumor tumor JJ cord-033493-kslzdy8q 133 31 activities activity NNS cord-033493-kslzdy8q 133 32 of of IN cord-033493-kslzdy8q 133 33 some some DT cord-033493-kslzdy8q 133 34 new new JJ cord-033493-kslzdy8q 133 35 pyridines pyridine NNS cord-033493-kslzdy8q 133 36 and and CC cord-033493-kslzdy8q 133 37 pyrazolo[1,5-a]pyrimidines pyrazolo[1,5-a]pyrimidines NNPS cord-033493-kslzdy8q 133 38 Cyanoacetanilides Cyanoacetanilides NNP cord-033493-kslzdy8q 133 39 intermediates intermediate NNS cord-033493-kslzdy8q 133 40 in in IN cord-033493-kslzdy8q 133 41 heterocyclic heterocyclic JJ cord-033493-kslzdy8q 133 42 synthesis synthesis NN cord-033493-kslzdy8q 133 43 . . . cord-033493-kslzdy8q 134 1 Part part NN cord-033493-kslzdy8q 134 2 5 5 CD cord-033493-kslzdy8q 134 3 : : : cord-033493-kslzdy8q 134 4 Preparation preparation NN cord-033493-kslzdy8q 134 5 of of IN cord-033493-kslzdy8q 134 6 hitherto hitherto VBD cord-033493-kslzdy8q 134 7 unknown unknown JJ cord-033493-kslzdy8q 134 8 5-aminopyrazole 5-aminopyrazole CD cord-033493-kslzdy8q 134 9 and and CC cord-033493-kslzdy8q 134 10 pyrazolo[1,5-a]pyrimidine pyrazolo[1,5-a]pyrimidine JJ cord-033493-kslzdy8q 134 11 derivatives derivative NNS cord-033493-kslzdy8q 134 12 containing contain VBG cord-033493-kslzdy8q 134 13 sulfamoyl sulfamoyl NNP cord-033493-kslzdy8q 134 14 moiety moiety NNP cord-033493-kslzdy8q 134 15 Synthesis Synthesis NNP cord-033493-kslzdy8q 134 16 of of IN cord-033493-kslzdy8q 134 17 some some DT cord-033493-kslzdy8q 134 18 new new JJ cord-033493-kslzdy8q 134 19 purine purine NN cord-033493-kslzdy8q 134 20 - - HYPH cord-033493-kslzdy8q 134 21 related relate VBN cord-033493-kslzdy8q 134 22 compounds compound NNS cord-033493-kslzdy8q 134 23 : : : cord-033493-kslzdy8q 135 1 Regioselective Regioselective NNP cord-033493-kslzdy8q 135 2 one one CD cord-033493-kslzdy8q 135 3 - - HYPH cord-033493-kslzdy8q 135 4 pot pot NN cord-033493-kslzdy8q 135 5 synthesis synthesis NN cord-033493-kslzdy8q 135 6 of of IN cord-033493-kslzdy8q 135 7 new new JJ cord-033493-kslzdy8q 135 8 tetrazolo[1,5-a]pyrimidine tetrazolo[1,5-a]pyrimidine NNP cord-033493-kslzdy8q 135 9 , , , cord-033493-kslzdy8q 135 10 pyrazolo[1,5-a]pyrimidine pyrazolo[1,5-a]pyrimidine NNP cord-033493-kslzdy8q 135 11 and and CC cord-033493-kslzdy8q 135 12 pyrimido[1,6-a]-pyrimidine pyrimido[1,6-a]-pyrimidine NNP cord-033493-kslzdy8q 136 1 derivatives derivative NNS cord-033493-kslzdy8q 136 2 Novel Novel NNP cord-033493-kslzdy8q 136 3 synthesis synthesis NN cord-033493-kslzdy8q 136 4 of of IN cord-033493-kslzdy8q 136 5 some some DT cord-033493-kslzdy8q 136 6 new new JJ cord-033493-kslzdy8q 136 7 pyrimido[1,6-a]pyrimidine pyrimido[1,6-a]pyrimidine NN cord-033493-kslzdy8q 136 8 and and CC cord-033493-kslzdy8q 136 9 pyrazolo[1,5-a]pyrimidine pyrazolo[1,5-a]pyrimidine JJ cord-033493-kslzdy8q 136 10 derivatives derivative NNS cord-033493-kslzdy8q 136 11 Synthesis Synthesis NNP cord-033493-kslzdy8q 136 12 and and CC cord-033493-kslzdy8q 137 1 in in IN cord-033493-kslzdy8q 137 2 vitro vitro FW cord-033493-kslzdy8q 137 3 cytotoxic cytotoxic JJ cord-033493-kslzdy8q 137 4 activity activity NN cord-033493-kslzdy8q 137 5 of of IN cord-033493-kslzdy8q 137 6 novel novel NN cord-033493-kslzdy8q 137 7 pyrazolo[1,5-a]pyrimidines pyrazolo[1,5-a]pyrimidine NNS cord-033493-kslzdy8q 137 8 and and CC cord-033493-kslzdy8q 137 9 related relate VBN cord-033493-kslzdy8q 137 10 Schiff Schiff NNP cord-033493-kslzdy8q 137 11 bases basis NNS cord-033493-kslzdy8q 137 12 Synthesis Synthesis NNP cord-033493-kslzdy8q 137 13 , , , cord-033493-kslzdy8q 137 14 Characterization characterization NN cord-033493-kslzdy8q 137 15 , , , cord-033493-kslzdy8q 137 16 and and CC cord-033493-kslzdy8q 137 17 Cytotoxicity Cytotoxicity NNP cord-033493-kslzdy8q 137 18 of of IN cord-033493-kslzdy8q 137 19 some some DT cord-033493-kslzdy8q 137 20 new new JJ cord-033493-kslzdy8q 137 21 5-aminopyrazole 5-aminopyrazole CD cord-033493-kslzdy8q 137 22 and and CC cord-033493-kslzdy8q 137 23 pyrazolo[1,5-a]pyrimidine pyrazolo[1,5-a]pyrimidine NNP cord-033493-kslzdy8q 138 1 derivatives derivative NNS cord-033493-kslzdy8q 138 2 Synthesis Synthesis NNP cord-033493-kslzdy8q 138 3 and and CC cord-033493-kslzdy8q 138 4 antitumor antitumor JJ cord-033493-kslzdy8q 138 5 activity activity NN cord-033493-kslzdy8q 138 6 of of IN cord-033493-kslzdy8q 138 7 some some DT cord-033493-kslzdy8q 138 8 new new JJ cord-033493-kslzdy8q 138 9 pyrazolo[1,5-a]pyrimidines pyrazolo[1,5-a]pyrimidines NNPS cord-033493-kslzdy8q 138 10 Synthesis Synthesis NNP cord-033493-kslzdy8q 138 11 , , , cord-033493-kslzdy8q 138 12 Structural Structural NNP cord-033493-kslzdy8q 138 13 Elucidation Elucidation NNP cord-033493-kslzdy8q 138 14 , , , cord-033493-kslzdy8q 138 15 and and CC cord-033493-kslzdy8q 138 16 in in IN cord-033493-kslzdy8q 138 17 vitro vitro FW cord-033493-kslzdy8q 138 18 Antitumor Antitumor NNP cord-033493-kslzdy8q 138 19 Activities Activities NNPS cord-033493-kslzdy8q 138 20 of of IN cord-033493-kslzdy8q 138 21 Some some DT cord-033493-kslzdy8q 138 22 Pyrazolopyrimidines Pyrazolopyrimidines NNPS cord-033493-kslzdy8q 138 23 and and CC cord-033493-kslzdy8q 138 24 schiff schiff NNP cord-033493-kslzdy8q 138 25 bases basis NNS cord-033493-kslzdy8q 138 26 derived derive VBN cord-033493-kslzdy8q 138 27 from from IN cord-033493-kslzdy8q 138 28 5-amino-3-(arylamino)-1H 5-amino-3-(arylamino)-1h CD cord-033493-kslzdy8q 138 29 - - HYPH cord-033493-kslzdy8q 138 30 pyrazole-4-carboxamides pyrazole-4-carboxamides NNP cord-033493-kslzdy8q 138 31 Synthesis Synthesis NNP cord-033493-kslzdy8q 138 32 and and CC cord-033493-kslzdy8q 138 33 in in IN cord-033493-kslzdy8q 138 34 vitro vitro FW cord-033493-kslzdy8q 138 35 anticancer anticancer JJ cord-033493-kslzdy8q 138 36 activity activity NN cord-033493-kslzdy8q 138 37 of of IN cord-033493-kslzdy8q 138 38 pyrazolo pyrazolo NNP cord-033493-kslzdy8q 138 39 Synthesis Synthesis NNP cord-033493-kslzdy8q 138 40 of of IN cord-033493-kslzdy8q 138 41 structurally structurally RB cord-033493-kslzdy8q 138 42 related relate VBN cord-033493-kslzdy8q 138 43 purines purine NNS cord-033493-kslzdy8q 138 44 : : : cord-033493-kslzdy8q 138 45 Benzimidazo[1,2-a]pyridines benzimidazo[1,2-a]pyridine NNS cord-033493-kslzdy8q 138 46 , , , cord-033493-kslzdy8q 138 47 benzimidazo-[1,2-c]-pyrimidines benzimidazo-[1,2-c]-pyrimidines CD cord-033493-kslzdy8q 138 48 , , , cord-033493-kslzdy8q 138 49 and and CC cord-033493-kslzdy8q 138 50 pyrazolo-[1,5-a]pyrimidines pyrazolo-[1,5-a]pyrimidines NNP cord-033493-kslzdy8q 138 51 1,2,3,4-Tetrahydrobenzimidazo[2,1-b]-quinazoline 1,2,3,4-tetrahydrobenzimidazo[2,1-b]-quinazoline CD cord-033493-kslzdy8q 138 52 1,2-Dimethylpyrido[1,2-a]benzimidazole-4-carbonitrile 1,2-dimethylpyrido[1,2-a]benzimidazole-4-carbonitrile CD cord-033493-kslzdy8q 139 1 Antimetabolites Antimetabolites NNPS cord-033493-kslzdy8q 139 2 : : : cord-033493-kslzdy8q 140 1 A a DT cord-033493-kslzdy8q 140 2 novel novel JJ cord-033493-kslzdy8q 140 3 synthesis synthesis NN cord-033493-kslzdy8q 140 4 of of IN cord-033493-kslzdy8q 140 5 nonclassical nonclassical JJ cord-033493-kslzdy8q 140 6 condensed condense VBN cord-033493-kslzdy8q 140 7 carbocyclic carbocyclic JJ cord-033493-kslzdy8q 140 8 purine purine NNP cord-033493-kslzdy8q 140 9 analogues analogue NNS cord-033493-kslzdy8q 140 10 . . . cord-033493-kslzdy8q 141 1 Egypt Egypt NNP cord-033493-kslzdy8q 141 2 Novel Novel NNP cord-033493-kslzdy8q 141 3 purine purine NN cord-033493-kslzdy8q 141 4 thioglycoside thioglycoside IN cord-033493-kslzdy8q 141 5 analogs analog NNS cord-033493-kslzdy8q 141 6 : : : cord-033493-kslzdy8q 142 1 Synthesis synthesis NN cord-033493-kslzdy8q 142 2 , , , cord-033493-kslzdy8q 142 3 nanoformulation nanoformulation NN cord-033493-kslzdy8q 142 4 and and CC cord-033493-kslzdy8q 142 5 biological biological JJ cord-033493-kslzdy8q 142 6 evaluation evaluation NN cord-033493-kslzdy8q 142 7 in in IN cord-033493-kslzdy8q 142 8 in in FW cord-033493-kslzdy8q 142 9 vitro vitro FW cord-033493-kslzdy8q 142 10 human human JJ cord-033493-kslzdy8q 142 11 liver liver NN cord-033493-kslzdy8q 142 12 and and CC cord-033493-kslzdy8q 142 13 breast breast NN cord-033493-kslzdy8q 142 14 cancer cancer NN cord-033493-kslzdy8q 142 15 models model NNS cord-033493-kslzdy8q 143 1 Antimetabolites Antimetabolites NNPS cord-033493-kslzdy8q 143 2 : : : cord-033493-kslzdy8q 143 3 Design design NN cord-033493-kslzdy8q 143 4 , , , cord-033493-kslzdy8q 143 5 synthesis synthesis NN cord-033493-kslzdy8q 143 6 , , , cord-033493-kslzdy8q 143 7 and and CC cord-033493-kslzdy8q 143 8 cytotoxic cytotoxic JJ cord-033493-kslzdy8q 143 9 evaluation evaluation NN cord-033493-kslzdy8q 143 10 of of IN cord-033493-kslzdy8q 143 11 novel novel NNP cord-033493-kslzdy8q 143 12 dihydropyridine dihydropyridine NNP cord-033493-kslzdy8q 143 13 thioglycosides thioglycosides NNP cord-033493-kslzdy8q 143 14 and and CC cord-033493-kslzdy8q 143 15 pyridine pyridine NNP cord-033493-kslzdy8q 143 16 thioglycosides thioglycosides NNP cord-033493-kslzdy8q 143 17 Crystal Crystal NNP cord-033493-kslzdy8q 143 18 structure structure NN cord-033493-kslzdy8q 143 19 of of IN cord-033493-kslzdy8q 143 20 1-amino-2-oxo-2,5,6,7,8,9-hexahydro-1H 1-amino-2-oxo-2,5,6,7,8,9-hexahydro-1h CD cord-033493-kslzdy8q 143 21 - - HYPH cord-033493-kslzdy8q 143 22 cyclohepta cyclohepta NN cord-033493-kslzdy8q 143 23 New new JJ cord-033493-kslzdy8q 143 24 synthetic synthetic JJ cord-033493-kslzdy8q 143 25 strategies strategy NNS cord-033493-kslzdy8q 143 26 for for IN cord-033493-kslzdy8q 143 27 acyclic acyclic JJ cord-033493-kslzdy8q 143 28 and and CC cord-033493-kslzdy8q 143 29 cyclic cyclic JJ cord-033493-kslzdy8q 143 30 pyrimidinethione pyrimidinethione NNP cord-033493-kslzdy8q 143 31 nucleosides nucleoside NNS cord-033493-kslzdy8q 143 32 and and CC cord-033493-kslzdy8q 143 33 their -PRON- PRP$ cord-033493-kslzdy8q 143 34 analogues analogue NNS cord-033493-kslzdy8q 143 35 Design Design NNP cord-033493-kslzdy8q 143 36 , , , cord-033493-kslzdy8q 143 37 synthesis synthesis NN cord-033493-kslzdy8q 143 38 , , , cord-033493-kslzdy8q 143 39 molecular molecular JJ cord-033493-kslzdy8q 143 40 docking docking NN cord-033493-kslzdy8q 143 41 and and CC cord-033493-kslzdy8q 143 42 anti anti JJ cord-033493-kslzdy8q 143 43 - - JJ cord-033493-kslzdy8q 143 44 hepatocellular hepatocellular JJ cord-033493-kslzdy8q 143 45 carcinoma carcinoma NN cord-033493-kslzdy8q 143 46 evaluation evaluation NN cord-033493-kslzdy8q 143 47 of of IN cord-033493-kslzdy8q 143 48 novel novel JJ cord-033493-kslzdy8q 143 49 acyclic acyclic NNP cord-033493-kslzdy8q 143 50 pyridine pyridine NN cord-033493-kslzdy8q 143 51 thioglycosides thioglycosides NNP cord-033493-kslzdy8q 144 1 A a DT cord-033493-kslzdy8q 144 2 direct direct JJ cord-033493-kslzdy8q 144 3 route route NN cord-033493-kslzdy8q 144 4 to to IN cord-033493-kslzdy8q 144 5 a a DT cord-033493-kslzdy8q 144 6 new new JJ cord-033493-kslzdy8q 144 7 class class NN cord-033493-kslzdy8q 144 8 of of IN cord-033493-kslzdy8q 144 9 acrylamide acrylamide NN cord-033493-kslzdy8q 144 10 thioglycosides thioglycosides NNP cord-033493-kslzdy8q 144 11 Rapid Rapid NNP cord-033493-kslzdy8q 144 12 colorimetric colorimetric JJ cord-033493-kslzdy8q 144 13 assay assay NN cord-033493-kslzdy8q 144 14 for for IN cord-033493-kslzdy8q 144 15 cellular cellular JJ cord-033493-kslzdy8q 144 16 growth growth NN cord-033493-kslzdy8q 144 17 and and CC cord-033493-kslzdy8q 144 18 survival survival NN cord-033493-kslzdy8q 144 19 : : : cord-033493-kslzdy8q 144 20 Application application NN cord-033493-kslzdy8q 144 21 to to IN cord-033493-kslzdy8q 144 22 proliferation proliferation NN cord-033493-kslzdy8q 144 23 and and CC cord-033493-kslzdy8q 144 24 cytotoxicity cytotoxicity NN cord-033493-kslzdy8q 144 25 assays assay NNS cord-033493-kslzdy8q 144 26 Plaque Plaque NNP cord-033493-kslzdy8q 144 27 inhibition inhibition NN cord-033493-kslzdy8q 144 28 assay assay NN cord-033493-kslzdy8q 144 29 for for IN cord-033493-kslzdy8q 144 30 drug drug NN cord-033493-kslzdy8q 144 31 susceptibility susceptibility NN cord-033493-kslzdy8q 144 32 testing testing NN cord-033493-kslzdy8q 144 33 of of IN cord-033493-kslzdy8q 144 34 influenza influenza NN cord-033493-kslzdy8q 144 35 viruses virus NNS cord-033493-kslzdy8q 144 36 Synthesis synthesis NN cord-033493-kslzdy8q 144 37 and and CC cord-033493-kslzdy8q 144 38 screening screening NN cord-033493-kslzdy8q 144 39 of of IN cord-033493-kslzdy8q 144 40 some some DT cord-033493-kslzdy8q 144 41 novel novel NN cord-033493-kslzdy8q 144 42 fused fuse VBN cord-033493-kslzdy8q 144 43 thiophene thiophene NNP cord-033493-kslzdy8q 144 44 and and CC cord-033493-kslzdy8q 144 45 thienopyrimidine thienopyrimidine JJ cord-033493-kslzdy8q 144 46 derivatives derivative NNS cord-033493-kslzdy8q 144 47 for for IN cord-033493-kslzdy8q 144 48 anti anti JJ cord-033493-kslzdy8q 144 49 - - JJ cord-033493-kslzdy8q 144 50 avian avian JJ cord-033493-kslzdy8q 144 51 influenza influenza NN cord-033493-kslzdy8q 144 52 virus virus NN cord-033493-kslzdy8q 144 53 ( ( -LRB- cord-033493-kslzdy8q 144 54 H5N1 H5N1 NNP cord-033493-kslzdy8q 144 55 ) ) -RRB- cord-033493-kslzdy8q 144 56 activity activity NN cord-033493-kslzdy8q 144 57 Synthesis Synthesis NNP cord-033493-kslzdy8q 144 58 and and CC cord-033493-kslzdy8q 144 59 anti anti JJ cord-033493-kslzdy8q 144 60 - - JJ cord-033493-kslzdy8q 144 61 proliferative proliferative JJ cord-033493-kslzdy8q 144 62 activity activity NN cord-033493-kslzdy8q 144 63 of of IN cord-033493-kslzdy8q 144 64 novel novel NN cord-033493-kslzdy8q 144 65 oxepin oxepin NNP cord-033493-kslzdy8q 144 66 - - HYPH cord-033493-kslzdy8q 144 67 annulated annulate VBN cord-033493-kslzdy8q 144 68 coumarins coumarins NNP cord-033493-kslzdy8q 144 69 Protocols protocol NNS cord-033493-kslzdy8q 144 70 for for IN cord-033493-kslzdy8q 144 71 screening screen VBG cord-033493-kslzdy8q 144 72 chemical chemical JJ cord-033493-kslzdy8q 144 73 agents agent NNS cord-033493-kslzdy8q 144 74 and and CC cord-033493-kslzdy8q 144 75 natural natural JJ cord-033493-kslzdy8q 144 76 products product NNS cord-033493-kslzdy8q 144 77 against against IN cord-033493-kslzdy8q 144 78 animal animal NN cord-033493-kslzdy8q 144 79 tumors tumor NNS cord-033493-kslzdy8q 144 80 and and CC cord-033493-kslzdy8q 144 81 other other JJ cord-033493-kslzdy8q 144 82 biological biological JJ cord-033493-kslzdy8q 144 83 systems system NNS cord-033493-kslzdy8q 144 84 Toward toward IN cord-033493-kslzdy8q 144 85 developing develop VBG cord-033493-kslzdy8q 144 86 therapies therapy NNS cord-033493-kslzdy8q 144 87 against against IN cord-033493-kslzdy8q 144 88 corona corona NN cord-033493-kslzdy8q 144 89 virus virus NN cord-033493-kslzdy8q 144 90 : : : cord-033493-kslzdy8q 144 91 synthesis synthesis NN cord-033493-kslzdy8q 144 92 and and CC cord-033493-kslzdy8q 144 93 anti anti JJ cord-033493-kslzdy8q 144 94 - - JJ cord-033493-kslzdy8q 144 95 avian avian JJ cord-033493-kslzdy8q 144 96 influenza influenza NN cord-033493-kslzdy8q 144 97 virus virus NN cord-033493-kslzdy8q 144 98 activity activity NN cord-033493-kslzdy8q 144 99 of of IN cord-033493-kslzdy8q 144 100 novel novel NN cord-033493-kslzdy8q 144 101 cytosine cytosine NN cord-033493-kslzdy8q 144 102 thioglycoside thioglycoside NNP cord-033493-kslzdy8q 144 103 analogues analogue NNS