Synthesis, antiviral activity, and stability of nucleoside analogs containing tricyclic bases

Eur J Med Chem. 2009 Oct;44(10):3845-51. doi: 10.1016/j.ejmech.2009.04.003. Epub 2009 Apr 8.

Abstract

A series of 3,9-dihydro-9-oxo-5H-imidazo[1,2-A]purine nucleosides (tricylic nucleosides) were synthesized from 9-[4-alpha-(hydroxymethyl)cyclopent-2-ene-1-alpha-yl]guanine (CBV) 5, (-)-beta-D-(2R,4R)-1,3-dioxolane-guanosine (DXG) 6, 3'-azido-3'-deoxy-guanosine (AZG) 7, and 2'-C-methylguanosine 8. Their in vitro activity against HIV and HCV was evaluated and correlated to their ability to degrade to their purine counterpart.

Publication types

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

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Antiviral Agents / toxicity
  • Cell Survival / drug effects
  • Cells, Cultured
  • Chlorocebus aethiops
  • HIV / drug effects*
  • Hepacivirus / drug effects*
  • Herpesvirus 1, Human / drug effects
  • Humans
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Nucleosides / pharmacology*
  • Nucleosides / toxicity
  • Vero Cells

Substances

  • Antiviral Agents
  • Nucleosides