A facile synthesis of 5'-fluoro-5'-deoxyacadesine (5'-F-AICAR): a novel non-phosphorylable AICAR analogue

Molecules. 2012 Nov 2;17(11):13036-44. doi: 10.3390/molecules171113036.

Abstract

The substitution of a hydroxyl group by a fluorine atom in a potential drug is an efficient reaction that can, in principle, improve its pharmacological properties. Herein, the synthesis of the novel compound 5'-fluoro-5'-deoxyacadesine (5'-F-AICAR), a strict analogue of AICAR that cannot be 5'-phosphorylated to ZMP by cellular kinases, is reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enzyme Activators / chemical synthesis*
  • Halogenation
  • Phosphorylation
  • Purine Nucleosides / chemistry
  • Ribonucleosides / chemical synthesis*

Substances

  • 5'-fluoro-5'-deoxyacadesine
  • Enzyme Activators
  • Purine Nucleosides
  • Ribonucleosides