Synthesis and biological evaluation of (3'S)-3'-deoxy-3'-fluoro-3'-C-ethynylcytidine

Nucleosides Nucleotides Nucleic Acids. 2012 Apr;31(4):286-92. doi: 10.1080/15257770.2011.652753.

Abstract

The novel pyrimidine nucleoside, (3'S)-3'-deoxy-3'-fluoro-3'-C-ethynylcytidine (1) was synthesized from cytidine in seven steps. The key step in the synthesis was the introduction of the tertiary fluorine at the 3'-position. Compound 1 was evaluated in vitro against several RNA viruses.

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Deoxycytidine / analogs & derivatives*
  • Deoxycytidine / chemical synthesis
  • Deoxycytidine / chemistry
  • Deoxycytidine / pharmacology
  • Humans
  • Microbial Sensitivity Tests
  • Pyrimidine Nucleosides / chemical synthesis*
  • Pyrimidine Nucleosides / chemistry
  • Pyrimidine Nucleosides / pharmacology*
  • RNA Viruses / drug effects*

Substances

  • Antiviral Agents
  • Pyrimidine Nucleosides
  • Deoxycytidine