Stereocontrolled synthesis and biological activity of two diastereoisomers of the potent HIV-1 protease inhibitor saquinavir

Bioorg Med Chem. 2008 Jan 15;16(2):902-8. doi: 10.1016/j.bmc.2007.10.020. Epub 2007 Oct 12.

Abstract

A general enantioselective synthesis of new syn-hydroxyethylamine isosteres has been developed. The approach, based on the controlled opening of functionalized optically active 2,3-epoxy amines, can be conveniently used for the preparation of new peptidomimetics with various residues. Finally the total synthesis of two diastereoisomer analogues of HIV-Protease inhibitor Saquinavir has been achieved and their biological activity evaluated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques
  • HIV Protease Inhibitors* / chemical synthesis
  • HIV Protease Inhibitors* / chemistry
  • HIV Protease Inhibitors* / pharmacology
  • HIV-1 / drug effects*
  • Inhibitory Concentration 50
  • Molecular Mimicry
  • Molecular Structure
  • Peptides / chemical synthesis
  • Peptides / chemistry*
  • Peptides / pharmacology
  • Saquinavir* / analogs & derivatives
  • Saquinavir* / chemical synthesis
  • Saquinavir* / chemistry
  • Saquinavir* / pharmacology
  • Stereoisomerism

Substances

  • HIV Protease Inhibitors
  • Peptides
  • Saquinavir