Synthesis and antiviral activity of 2'-fluorohexopyranosyl nucleosides

Arch Pharm Res. 1998 Jun;21(3):338-43. doi: 10.1007/BF02975298.

Abstract

2'-Fluorohexopyranosyl nucleosides 1a and 1b which contained a bioisosteric double bond and a fluorine were synthesized in 12 steps, starting from D-galactose. During diethylaminosulfur trifluoride (DAST) fluorination, retention of stereochemistry was observed through the participation of methoxy or chloro group at the 6-position of the purine base. The final nucleosides 1a and 1b were found to be inactive against HIV-1 and HSV-1,2.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis
  • Adenosine / pharmacology
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • HIV-1 / drug effects
  • Herpesvirus 1, Human / drug effects
  • Herpesvirus 2, Human / drug effects
  • Magnetic Resonance Spectroscopy

Substances

  • Antiviral Agents
  • Adenosine