Synthesis and anti-HIV activity of [ddN]-[ddN] dimers and benzimidazole nucleoside dimers

Chem Biodivers. 2009 Dec;6(12):2200-8. doi: 10.1002/cbdv.200800281.

Abstract

In an attempt to combine the HIV-inhibitory capacity of different 2',3'-dideoxynucleoside (ddN) analogs, we have designed and synthesized several dimers of [AZT]-[AZT] and [AZT]-[d4T]. In addition, we also synthesized the dimers of 1-(1H-benzimidazol-1-yl)-1-deoxy-beta-D-ribofuranose. The in vitro anti-HIV activity of these compounds on a pseudotype virus, pNL4-3.Luc.R-E-, in the 293T cells has been determined. Among these compounds, 2,2'-(propane-1,3-diyl)bis[1-(beta-D-ribofuranosyl)-1H-benzimidazole] showed the highest anti-HIV activity with similar effect as AZT.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry*
  • Benzimidazoles / pharmacology
  • Cell Line
  • Dideoxynucleosides / chemical synthesis
  • Dideoxynucleosides / chemistry*
  • Dideoxynucleosides / pharmacology
  • Dimerization
  • HIV Core Protein p24 / metabolism
  • Humans
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Nucleosides / pharmacology
  • Zidovudine / chemistry

Substances

  • 2,2'-(propane-1,3-diyl)bis(1-(ribofuranosyl)-1H-benzimidazole)
  • Anti-HIV Agents
  • Benzimidazoles
  • Dideoxynucleosides
  • HIV Core Protein p24
  • Nucleosides
  • Zidovudine
  • benzimidazole