Synthesis and antiviral evaluation of 2'-deoxy-2'-C-trifiuoromethyl beta-D-ribonucleoside analogues bearing the five naturally occurring nucleic acid bases

Org Biomol Chem. 2003 Jun 21;1(12):2096-102. doi: 10.1039/b303093h.

Abstract

2'-Deoxy-2'-C-trifluoromethyl-beta-D-ribonucleoside derivatives bearing the five naturally occurring acid bases have been synthesized. All these derivatives were prepared by glycosylation reactions of purine and pyrimidine bases with a suitable peracylated 2-deoxy-2-C-trifluoromethyl sugar precursor to afford anomeric mixtures of protected nucleosides. After separation and deprotection, the resulting beta-nucleoside analogues were tested for their activity against HIV, HBV and several RNA viruses. However, none of these compounds showed significant antiviral activity nor cytotoxicity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Deoxyribonucleosides / chemical synthesis*
  • Deoxyribonucleosides / pharmacology
  • Glycosylation
  • HIV / drug effects
  • Hepatitis B virus / drug effects
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Hydrocarbons, Fluorinated / pharmacology
  • Purines / chemistry
  • Pyrimidines / chemistry
  • RNA Viruses / drug effects

Substances

  • Antiviral Agents
  • Deoxyribonucleosides
  • Hydrocarbons, Fluorinated
  • Purines
  • Pyrimidines