Synthesis and biological activity of certain 1,2,3-triazole carboxamide nucleosides related to bredinin and pyrazofurin.
5-Hydroxy-1-(beta-D-ribofuranosyl)-1,2,3-triazole-4-carboxamide (II) has been prepared by direct glycosylation of the trimethylsilyl derivative of 5-hydroxy-1,2,3-triazole-4-carboxamide (IV). The use of trimethylsilyltrifluoromethane sulfonate as a catalyst and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose in acetonitrile gave a 95% yield of a 1:1 mixture of V and VI as blocked nucleosides which were readily separated on a silica gel column. The synthesis of II was also achieved by the cycloaddition of 2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl azide with ethyl malonamate. II shows significant antiviral activity against herpes and measles virus in vitro.
D000577:Amides; D000818:Animals; D002286:Carcinoma, Ehrlich Tumor / Q000201:enzymology; D004353:Drug Evaluation, Preclinical; D007168:IMP Dehydrogenase / Q000037:antagonists & inhibitors; D051379:Mice; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D011720:Pyrazoles; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D012266:Ribose; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000138:chemical synthesis / Q000494:pharmacology
D000577:Amides; D009705:Nucleosides; D011720:Pyrazoles; D012263:Ribonucleosides; D014230:Triazoles; C002997:pyrazofurin; C010052:mizoribine; C032449:5-hydroxy-1-(beta-D-ribofuranosyl)-1,2,3-triazole-4-carboxamide; D012266:Ribose; D007168:IMP Dehydrogenase