Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors possessing augmented P2' side chains

Bioorg Med Chem Lett. 2006 Feb 15;16(4):859-63. doi: 10.1016/j.bmcl.2005.11.011. Epub 2005 Nov 18.

Abstract

A series of monopyrrolinone-based HIV-1 protease inhibitors possessing rationally designed P2' side chains have been synthesized and evaluated for activity against wild-type HIV-1 protease. The most potent inhibitor displays subnanomolar potency in vitro for the wild-type HIV-1 protease. Additionally, the monopyrrolinone inhibitors retain potency in cellular assays against clinically significant mutant forms of the virus. X-ray structures of these inhibitors bound in the wild-type enzyme reveal important insights into the observed biological activity.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cattle
  • Crystallography, X-Ray
  • Drug Design
  • HIV Protease / drug effects*
  • HIV Protease Inhibitors* / chemical synthesis
  • HIV Protease Inhibitors* / chemistry
  • HIV Protease Inhibitors* / pharmacology
  • Humans
  • In Vitro Techniques
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Mutation
  • Pyrrolidinones* / chemical synthesis
  • Pyrrolidinones* / chemistry
  • Pyrrolidinones* / pharmacology
  • Structure-Activity Relationship

Substances

  • HIV Protease Inhibitors
  • Pyrrolidinones
  • HIV Protease