title: Synthesis of N3,5'-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridin-5-one and its 3'-deoxysugar analogue as potential anti-hepatitis C virus agents.
abstract: We recently discovered a novel compound, identified as N3, 5-cyclo-4-(beta-D-ribofuranosyl)-vic-triazolo[4,5-b]pyridinin-5-one, with anti-hepatitis C virus (HCV) activity in vitro. The structure was confirmed by chemical synthesis from 2-hydroxy-5-nitropyridine. It showed anti-HCV activity with EC50= 19.7 microM in replicon cells. Its 3'-deoxy sugar analogue was also synthesized, but was inactive against HCV in vitro.
authors.affiliation: Department of Chemistry, Pharmasset, Inc., Tucker, GA 30084, USA.
authors.forename: Peiyuan
authors.initials: P
authors.lastname: Wang
authors.forename: Laurent
authors.initials: L
authors.lastname: Hollecker
authors.forename: Krzysztof W
authors.initials: KW
authors.lastname: Pankiewicz
authors.forename: Steven E
authors.initials: SE
authors.lastname: Patterson
authors.forename: Tony
authors.initials: T
authors.lastname: Whitaker
authors.forename: Tamara R
authors.initials: TR
authors.lastname: McBrayer
authors.forename: Phillip M
authors.initials: PM
authors.lastname: Tharnish
authors.forename: Lieven J
authors.initials: LJ
authors.lastname: Stuyver
authors.forename: Raymond F
authors.initials: RF
authors.lastname: Schinazi
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Otto
authors.forename: Kyoichi A
authors.initials: KA
authors.lastname: Watanabe
mesh_terms: D000998:Antiviral Agents / Q000494:pharmacology; D002241:Carbohydrates / Q000737:chemistry; D012321:DNA-Directed RNA Polymerases / Q000737:chemistry; D003837:Deoxy Sugars / Q000737:chemistry; D016679:Genome, Viral; D016174:Hepacivirus / Q000235:genetics / Q000378:metabolism*; D006526:Hepatitis C / Q000188:drug therapy*; D006801:Humans; D008956:Models, Chemical; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D012263:Ribonucleosides / Q000737:chemistry; D017361:Viral Nonstructural Proteins / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D002241:Carbohydrates; D003837:Deoxy Sugars; C494561:N3,5'-cyclo-4-ribofuranosyl-vic-triazolo(4,5-b)pyridin-5-one; D009705:Nucleosides; D012263:Ribonucleosides; D017361:Viral Nonstructural Proteins; D012321:DNA-Directed RNA Polymerases