Synthesis and anti-HIV activity of new C2 symmetric derivatives designed as HIV-1 protease inhibitors

Farmaco. 2003 Feb;58(2):149-57. doi: 10.1016/s0014-827x(02)00016-2.

Abstract

The synthesis of several new anti-HIV-1 compounds is described. The new compounds contain a C(2) symmetry axis and a dihidroxyethylene moiety based on the D-tartaric acid back bone. The synthesis of these compounds was achieved in 36-69% overall yields from D-tartaric acid. The protocol included: acetylation of hydroxyl groups, followed by diamide formation and deacetylation or reduction with LiAlH(4). The anti-HIV 1 activities of these substances were evaluated in PM-1 cells, using Indinavir as standard (IC(50) = 0.2 microM). Two amino alcohol derivatives showed good inhibitory activity against the virus, with IC(50) = 2.0 and 4 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology
  • Carbon*
  • Cell Line
  • HIV Protease / metabolism
  • HIV Protease Inhibitors / chemical synthesis*
  • HIV Protease Inhibitors / chemistry
  • HIV Protease Inhibitors / pharmacology
  • HIV-1 / drug effects*
  • Humans

Substances

  • Anti-HIV Agents
  • HIV Protease Inhibitors
  • Carbon
  • HIV Protease