Solid-phase synthesis of a library based on biphenyl-containing trypsin-like serine protease inhibitors

Bioorg Med Chem Lett. 2009 Nov 15;19(22):6477-80. doi: 10.1016/j.bmcl.2009.08.100. Epub 2009 Sep 17.

Abstract

The solid-phase synthesis of a library based on an unusual biphenyl-containing trypsin-like serine protease inhibitor is described. Key to this effort was the synthesis of a highly functionalized aryl boronic acid reagent which required the development of a novel and efficient method to convert a triflate to a pinacolboronate in large scale.

MeSH terms

  • Aspartic Acid / pharmacology
  • Biphenyl Compounds / pharmacology*
  • HIV Protease Inhibitors / pharmacology
  • Mast Cells
  • Molecular Sequence Data
  • Peptide Library
  • Protease Inhibitors / chemistry*
  • Protease Inhibitors / pharmacology
  • Protein Conformation / drug effects
  • Serine / pharmacology
  • Serine Endopeptidases / drug effects*
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • Biphenyl Compounds
  • HIV Protease Inhibitors
  • Peptide Library
  • Protease Inhibitors
  • trypsin-like serine protease
  • diphenyl
  • Aspartic Acid
  • Serine
  • Serine Endopeptidases