Development of potent macrocyclic inhibitors of genotype 3a HCV NS3/4A protease

Bioorg Med Chem Lett. 2012 Dec 1;22(23):7201-6. doi: 10.1016/j.bmcl.2012.08.106. Epub 2012 Sep 7.

Abstract

A series of macrocyclic compounds containing 2-substituted-quinoline moieties have been discovered and shown to exhibit excellent HCV NS3/4a genotype 3a and genotype 1b R155K mutant activity while maintaining the high rat liver exposure. Cyclization of the 2-substituted quinoline substituent led to a series of tricyclic P2 compounds which also display superb gt3a potency.

MeSH terms

  • Animals
  • Carrier Proteins / antagonists & inhibitors*
  • Carrier Proteins / metabolism
  • Cyclization
  • Genotype
  • Half-Life
  • Hepacivirus / enzymology*
  • Hepacivirus / genetics
  • Intracellular Signaling Peptides and Proteins
  • Kinetics
  • Liver / metabolism
  • Macrocyclic Compounds / chemical synthesis
  • Macrocyclic Compounds / chemistry*
  • Macrocyclic Compounds / pharmacokinetics
  • Protease Inhibitors / chemical synthesis
  • Protease Inhibitors / chemistry*
  • Protease Inhibitors / pharmacokinetics
  • Quinolines / chemistry
  • Rats
  • Structure-Activity Relationship
  • Viral Nonstructural Proteins / antagonists & inhibitors*
  • Viral Nonstructural Proteins / metabolism

Substances

  • Carrier Proteins
  • Intracellular Signaling Peptides and Proteins
  • Macrocyclic Compounds
  • NS3 protein, hepatitis C virus
  • NS4A cofactor peptide, Hepatitis C virus
  • Protease Inhibitors
  • Quinolines
  • Viral Nonstructural Proteins
  • quinoline