Synthesis and studies of 3'-C-trifluoromethyl-beta-D-ribonucleosides bearing the five naturally occurring nucleic acid bases

Nucleosides Nucleotides Nucleic Acids. 2003 Dec;22(12):2195-202. doi: 10.1081/ncn-120026874.

Abstract

3'-C-Trifloromethyl-beta-D-ribonucleoside derivatives bearing the five naturally occurring nucleic acid bases have been synthesized. All these derivatives were prepared by glycosylation reactions of purine and pyrimidine bases with a suitable peracylated 3-C-trifluoromethyl ribofuranose precursor. After deprotection, the resulting title nucleoside analogues were tested for their inhibitory properties against the replication of HIV, HBV and several RNA viruses. However, none of these compounds showed significant antiviral activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Fluorine / chemistry*
  • Glycosylation
  • HIV / drug effects
  • Hepatitis B virus / drug effects
  • Humans
  • Microbial Sensitivity Tests
  • Purines / chemistry
  • Pyrimidines / chemistry
  • RNA Viruses / drug effects
  • Ribonucleosides / chemical synthesis*
  • Ribonucleosides / chemistry
  • Ribonucleosides / pharmacology

Substances

  • Antiviral Agents
  • Purines
  • Pyrimidines
  • Ribonucleosides
  • Fluorine