Synthesis and antiviral evaluation of unnatural beta-L-enantiomers of 3'-fluoro- and 3'-azido-2',3'-dideoxyguanosine derivatives

Nucleosides Nucleotides Nucleic Acids. 2000 Jan-Feb;19(1-2):205-17. doi: 10.1080/15257770008033004.

Abstract

3'-fluoro-2',3'-dideoxy- (3) and 3'-azido-2',3'-dideoxy- (4) beta-L-ribofuranonucleoside derivatives of guanine have been synthesized and their antiviral properties examined. All these derivatives were regioselectively and stereospecifically prepared by glycosylation of 2-N-acetyl-6-O-(diphenylcarbamoyl)guanine 5 with a suitable peracylated L-xylo-furanose sugar 6, followed by appropriate chemical modifications. The prepared compounds were tested for their activity against HIV and HBV viruses, but they did not show significant activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Cell Line
  • Dideoxynucleosides / chemical synthesis*
  • Dideoxynucleosides / chemistry
  • Dideoxynucleosides / pharmacology
  • Glycosylation
  • HIV-1 / drug effects
  • Hepatitis B virus / drug effects
  • Humans
  • Stereoisomerism
  • Virus Replication / drug effects

Substances

  • Anti-HIV Agents
  • Antiviral Agents
  • Dideoxynucleosides
  • 3'-azido-2',3'-dideoxyguanosine
  • 3'-fluoro-2',3'-dideoxyguanosine