A refined pharmacophore model for HIV-1 integrase inhibitors: Optimization of potency in the 1H-benzylindole series

Bioorg Med Chem Lett. 2008 May 1;18(9):2891-5. doi: 10.1016/j.bmcl.2008.03.089. Epub 2008 Apr 8.

Abstract

We report herein the development of a new three-dimensional pharmacophore model for HIV-1 integrase inhibitors which led to the discovery of some 4-[1-(4-fluorobenzyl)-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoic acids that are able to specifically inhibit the strand transfer step of integration at nanomolar concentration. The synthesis of the new designed molecules is also described.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butyrates / chemical synthesis
  • Butyrates / pharmacology*
  • Drug Design*
  • Drug Resistance, Viral
  • HIV Integrase / drug effects*
  • HIV Integrase / metabolism
  • HIV Integrase Inhibitors / chemical synthesis
  • HIV Integrase Inhibitors / pharmacology*
  • HIV-1 / drug effects*
  • HIV-1 / growth & development
  • Indoles / chemical synthesis
  • Indoles / pharmacology*
  • Models, Chemical
  • Structure-Activity Relationship

Substances

  • Butyrates
  • HIV Integrase Inhibitors
  • Indoles
  • HIV Integrase