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

Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):957-60. doi: 10.1081/ncn-200059314.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antiviral Agents / pharmacology
  • Carbohydrates / chemistry
  • DNA-Directed RNA Polymerases / chemistry
  • Deoxy Sugars / chemistry
  • Genome, Viral
  • Hepacivirus / genetics
  • Hepacivirus / metabolism*
  • Hepatitis C / drug therapy*
  • Humans
  • Models, Chemical
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Ribonucleosides / chemistry
  • Viral Nonstructural Proteins / chemistry

Substances

  • Antiviral Agents
  • Carbohydrates
  • Deoxy Sugars
  • N3,5'-cyclo-4-ribofuranosyl-vic-triazolo(4,5-b)pyridin-5-one
  • Nucleosides
  • Ribonucleosides
  • Viral Nonstructural Proteins
  • DNA-Directed RNA Polymerases