Discovery and characterization of substituted diphenyl heterocyclic compounds as potent and selective inhibitors of hepatitis C virus replication

Antimicrob Agents Chemother. 2008 Apr;52(4):1419-29. doi: 10.1128/AAC.00525-07. Epub 2008 Jan 28.

Abstract

A novel small-molecule inhibitor, referred to here as R706, was discovered in a high-throughput screen of chemical libraries against Huh-7-derived replicon cells carrying autonomously replicating subgenomic RNA of hepatitis C virus (HCV). R706 was highly potent in blocking HCV RNA replication as measured by real-time reverse transcription-PCR and Western blotting of R706-treated replicon cells. Structure-activity iterations of the R706 series yielded a lead compound, R803, that was more potent and highly specific for HCV replication, with no significant inhibitory activity against a panel of HCV-related positive-stranded RNA viruses. Furthermore, HCV genotype 1 replicons displayed markedly higher sensitivity to R803 treatment than a genotype 2a-derived replicon. In addition, R803 was tested by a panel of biochemical and cell-based assays for on-target and off-target activities, and the data suggested that the compound had a therapeutic window close to 100-fold, while its exact mechanism of action remained elusive. We found that R803 was more effective than alpha interferon (IFN-alpha) at blocking HCV RNA replication in the replicon model. In combination studies, R803 showed a weak synergistic effect with IFN-alpha/ribavirin but only additive effects with a protease inhibitor and an allosteric inhibitor of RNA-dependent RNA polymerase (20). We conclude that R803 and related heterocyclic compounds constitute a new class of HCV-specific inhibitors that could potentially be developed as a treatment for HCV infection.

Publication types

  • Evaluation Study

MeSH terms

  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Benzofurans / chemistry
  • Benzofurans / pharmacology
  • Cell Line, Tumor / drug effects
  • Cell Survival / drug effects
  • Drug Interactions
  • Drug Resistance, Viral
  • Genotype
  • Hepacivirus / classification
  • Hepacivirus / drug effects*
  • Hepacivirus / genetics
  • Hepacivirus / physiology
  • Heterocyclic Compounds / chemistry*
  • Heterocyclic Compounds / pharmacology*
  • Humans
  • Interferon-alpha / pharmacology
  • Microbial Sensitivity Tests / methods*
  • RNA, Viral / biosynthesis
  • Replicon / drug effects
  • Virus Replication / drug effects*

Substances

  • Antiviral Agents
  • Benzofurans
  • Heterocyclic Compounds
  • Interferon-alpha
  • RNA, Viral
  • enprofen