[Anti-AIDS thienopyrimidine nucleosides]

J Pharm Belg. 1995 Mar-Jun;50(2-3):121-61.
[Article in French]

Abstract

In response to the AIDS epidemic, the discovery of antiviral agents has been focused on the synthesis of nucleoside analogues. The basis moiety of these pyrimidine nucleosides were thieno and thiano[3,2-d]pyrimidine-2,4-dione possibly substituted on 7 position by methyl or aryl groups, 6,7-dihydrothieno[3,2-d]pyrimidin-4-one, bicyclic heterocycles including an uracil moiety. The first part of organic chemistry work has provided cyclic and acyclic N-nucleosides after adaptation of Vorbrüggen and Niedballa method. The carbohydrate fraction of these nucleosides included either a cyclic sugar yielding uridine, ARA U and IDU analogues or an hydroxylated chain that allowed access to aciclovir, ganciclovir and EBPU analogues. The second part has been devoted to functional arrangements beta-D-ribonucleoside respectively on carbohydrate and aglycon moieties carrying into reduction (synthesis of an unsaturated dideoxynucleoside, a d4T analogue) and amination reactions (cytidine analogue). Several compounds were tested against HIV1 in CEM cl 13 cell cultures, but none of them exhibited significant activity against this virus.

Publication types

  • English Abstract
  • Review

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • HIV-1 / drug effects*
  • Humans
  • Pyrimidine Nucleosides / chemical synthesis*
  • Pyrimidine Nucleosides / pharmacology

Substances

  • Antiviral Agents
  • Pyrimidine Nucleosides