Synthesis and evaluation of novel alpha-amino cyclic boronates as inhibitors of HCV NS3 protease

Bioorg Med Chem Lett. 2010 Jun 15;20(12):3550-6. doi: 10.1016/j.bmcl.2010.04.129. Epub 2010 May 20.


We have designed and synthesized a novel series of alpha-amino cyclic boronates and incorporated them successfully in several acyclic templates at the P1 position. These compounds are inhibitors of the HCV NS3 serine protease, and structural studies show that they inhibit the NS3 protease by trapping the Ser-139 hydroxyl group in the active site. Synthetic methodologies and SARs of this series of compounds are described.

MeSH terms

  • Boronic Acids / chemical synthesis*
  • Boronic Acids / pharmacology
  • Boronic Acids / therapeutic use
  • Catalytic Domain
  • Drug Design
  • Hepacivirus / drug effects*
  • Hepacivirus / enzymology
  • Molecular Structure
  • Serine / chemistry
  • Structure-Activity Relationship
  • Viral Nonstructural Proteins / antagonists & inhibitors*


  • Boronic Acids
  • NS3 protein, hepatitis C virus
  • Viral Nonstructural Proteins
  • Serine