Isothiazoles as active-site inhibitors of HCV NS5B polymerase

Bioorg Med Chem Lett. 2007 Jan 1;17(1):28-33. doi: 10.1016/j.bmcl.2006.10.002. Epub 2006 Oct 5.

Abstract

Isothiazole analogs were discovered as a novel class of active-site inhibitors of HCV NS5B polymerase. The best compound has an IC(50) of 200 nM and EC(50) of 100 nM, which is a significant improvement over the starting inhibitor (1). The X-ray complex structure of 1 with HCV NS5B was obtained at a resolution of 2.2A, revealing that the inhibitor is covalently linked with Cys 366 of the 'primer-grip'. Furthermore, it makes considerable contacts with the C-terminus, beta-loop, and more importantly, to the active-site of the enzyme. The uniqueness of this binding mode offers a new insight for the rational design of novel inhibitors for HCV NS5B polymerase.

MeSH terms

  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Binding Sites / drug effects
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Molecular Conformation
  • Protein Conformation
  • Thiazoles / chemistry*
  • Thiazoles / pharmacology*
  • Viral Nonstructural Proteins / antagonists & inhibitors*

Substances

  • 4-cyano-3-hydroxy-5-(3,5-bis(trifluoromethyl)benzylamino)isothiazole
  • Antiviral Agents
  • Enzyme Inhibitors
  • Thiazoles
  • Viral Nonstructural Proteins
  • NS-5 protein, hepatitis C virus