A facile synthesis of 4'-thio-arabinonucleosides as potential antiviral agents from D-glucose

Nucleic Acids Symp Ser. 1995:(34):21-2.

Abstract

As potential antiviral agents, 4'-thio-arabinonucleosides were synthesized. Methyl 3-O-benzyl-xylo-furanoside, readily obtained from D-glucose, was converted to 1,4-anhydro-4-deoxy-4-thio-arabinitol. The protection of hydroxyl groups and the Pummerer rearrangement, followed by Lewis acid induced glycosylation afforded 4'-thio-arabinonucleosides. The compounds showed anti HSV-1 activity.

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Arabinonucleosides / chemical synthesis*
  • Arabinonucleosides / chemistry
  • Arabinonucleosides / pharmacology
  • Drug Design
  • Glycosylation
  • Herpesvirus 1, Human / drug effects
  • Herpesvirus 2, Human / drug effects
  • Herpesvirus 3, Human / drug effects
  • Molecular Structure
  • Thionucleosides / chemical synthesis*
  • Thionucleosides / chemistry
  • Thionucleosides / pharmacology

Substances

  • Antiviral Agents
  • Arabinonucleosides
  • Thionucleosides