Synthesis of some benzimidazole derivatives endowed with 1,2,3-triazole as potential inhibitors of hepatitis C virus

Acta Pharm. 2016 Jun 1;66(2):219-31. doi: 10.1515/acph-2016-0014.

Abstract

New derivatives of 2-thiobenzimidazole incorporating triazole moiety were synthesized, characterized and tested in vitro for antiviral activity against hepatitis C virus (HCV) and hepatitis B virus (HBV). Their cytotoxicity was determined by the reduction in the number of viable cell. All of the synthesized compounds are inactive against HBV and some showed activity against HCV. In particular, two compounds showed significant activity, 2-{4-[(1-benzoylbenzimidazol-2-ylthio)methyl]-1H-1,2,3-triazol-1-yl}-N-(p-nitro-phenyl)-acetamide (13) and 2-(4-{[1-(p-chlorobenzoyl)-benzimidazol-2-ylthio)methyl]-1H-1,2,3-triazol-1-yl}-N-(p-nitrophenyl)-acetamide (17). The results give an insight into the importance of the substituent at position 2 of benzimidazole for the inhibition of HCV.

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology*
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / pharmacology*
  • Cell Survival / drug effects
  • DNA, Viral / genetics
  • Dose-Response Relationship, Drug
  • Drug Design
  • Hep G2 Cells
  • Hepacivirus / drug effects*
  • Hepacivirus / genetics
  • Hepacivirus / growth & development
  • Hepatocytes / drug effects
  • Hepatocytes / pathology
  • Hepatocytes / virology
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship
  • Time Factors
  • Triazoles / chemical synthesis*
  • Triazoles / pharmacology*
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Benzimidazoles
  • DNA, Viral
  • Triazoles
  • benzimidazole