Synthesis of novel potent hepatitis C virus NS3 protease inhibitors: discovery of 4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid as a N-acyl-L-hydroxyproline bioisostere

Bioorg Med Chem. 2007 Jan 15;15(2):827-38. doi: 10.1016/j.bmc.2006.10.044. Epub 2006 Oct 25.

Abstract

Potent tetrapeptidic inhibitors of the HCV NS3 protease have been developed incorporating 4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid as a new N-acyl-l-hydroxyproline mimic. The hydroxycyclopentene template was synthesized in eight steps from commercially available (syn)-tetrahydrophthalic anhydride. Three different amino acids were explored in the P1-position and in the P2-position the hydroxyl group of the cyclopentene template was substituted with 7-methoxy-2-phenyl-quinolin-4-ol. The P3/P4-positions were then optimized from a set of six amino acid derivatives. All inhibitors were evaluated in an in vitro assay using the full-length NS3 protease. Several potent inhibitors were identified, the most promising exhibiting a K(i) value of 1.1nM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclopentanes / chemical synthesis*
  • Cyclopentanes / pharmacology*
  • Dicarboxylic Acids / chemical synthesis*
  • Dicarboxylic Acids / pharmacology*
  • Indicators and Reagents
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Viral Nonstructural Proteins / antagonists & inhibitors*

Substances

  • 4-hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid
  • Cyclopentanes
  • Dicarboxylic Acids
  • Indicators and Reagents
  • NS3 protein, hepatitis C virus
  • Protease Inhibitors
  • Viral Nonstructural Proteins