Synthesis of 3'-deoxy-3'-C-methyl nucleoside derivatives

Bioorg Med Chem. 2008 Aug 1;16(15):7436-42. doi: 10.1016/j.bmc.2008.06.011. Epub 2008 Jun 13.

Abstract

2',3'-Dideoxy-3'-C-methyl nucleosides bearing the five naturally occurring nucleic acid bases were synthesized. Additionally, the 3'-deoxy-3'-C-methyl nucleoside analogues bearing 5-aminoimidazole-4-carboxamide as well as 1,2,4-triazole-3-carboxamide moieties were prepared. The synthesis of the corresponding 2',3'-dideoxy-3'-C-methyl triazole derivative was also accomplished. The dideoxynucleoside derivatives were prepared by radical deoxygenation from their 3'-deoxy-3'-C-methyl parent ribonucleosides. When evaluated for their antiviral activity in cell culture experiments, none of these compounds showed any significant antiviral activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology*
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Nucleosides