Design, Synthesis and Biological Evaluation of Peptidyl-Vinylaminophosphonates as Novel Cysteine Protease Inhibitors

Bioorg Med Chem. 2011 Dec 1;19(23):7129-35. doi: 10.1016/j.bmc.2011.09.058. Epub 2011 Oct 5.

Abstract

We report herein, design and synthesis of vinylaminophosphonates, a novel class of compounds as possible cysteine protease inhibitors. The synthesis of vinylaminophosphonates has been accomplished employing Tsuji-Trost reaction as a key step. The synthesized compounds were assayed against papain, a model cysteine protease and some of our synthesized compounds showed IC(50) values in the range of 30-54 μM thereby suggesting that these chemical entities thus could constitute an interesting template for the design of potential novel protease inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cysteine Proteinase Inhibitors / chemical synthesis
  • Cysteine Proteinase Inhibitors / chemistry*
  • Cysteine Proteinase Inhibitors / pharmacology
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Organophosphonates / chemical synthesis
  • Organophosphonates / chemistry*
  • Organophosphonates / pharmacology*
  • Peptides / chemical synthesis
  • Peptides / chemistry*
  • Peptides / pharmacology*
  • Spectroscopy, Fourier Transform Infrared
  • Structure-Activity Relationship
  • Vinyl Compounds / chemical synthesis
  • Vinyl Compounds / chemistry
  • Vinyl Compounds / pharmacology

Substances

  • Cysteine Proteinase Inhibitors
  • Organophosphonates
  • Peptides
  • Vinyl Compounds