Synthesis and antiviral activity of novel HCV NS3 protease inhibitors with P4 capping groups

Bioorg Med Chem Lett. 2012 Dec 15;22(24):7351-6. doi: 10.1016/j.bmcl.2012.10.075. Epub 2012 Oct 22.

Abstract

We have synthesized and evaluated a series of novel HCV NS3 protease inhibitors with various P4 capping groups, which include urea, carbamate, methoxy-carboxamide, cyclic carbamate and amide, pyruvic amide, oxamate, oxalamide and cyanoguanidine. Most of these compounds are remarkably potent, exhibiting single-digit to sub-nanomolar activity in the enzyme assay and cell-based replicon assay. Selected compounds were also evaluated in the protease-inhibitor-resistant mutant transient replicon assay, and they were found to show quite different potency profiles against a panel of HCV protease-inhibitor-resistant mutants.

MeSH terms

  • Amides / chemistry
  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Carbamates / chemistry
  • Dose-Response Relationship, Drug
  • Drug Resistance, Viral / genetics
  • Guanidines / chemistry
  • Hepacivirus / drug effects*
  • Hepacivirus / enzymology
  • Hepacivirus / genetics
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Oxamic Acid / chemistry
  • Rats
  • Serine Proteinase Inhibitors / chemical synthesis*
  • Serine Proteinase Inhibitors / chemistry
  • Serine Proteinase Inhibitors / pharmacology*
  • Structure-Activity Relationship
  • Urea / chemistry
  • Viral Nonstructural Proteins / antagonists & inhibitors*
  • Viral Nonstructural Proteins / metabolism

Substances

  • Amides
  • Antiviral Agents
  • Carbamates
  • Guanidines
  • NS3 protein, hepatitis C virus
  • Serine Proteinase Inhibitors
  • Viral Nonstructural Proteins
  • Urea
  • dicyandiamido
  • Oxamic Acid