7-deazainosine derivatives: synthesis and characterization of 7- and 7,8-substituted pyrrolo [2,3-d]pyrimidine ribonucleosides

Nucleosides Nucleotides Nucleic Acids. 2008 May;27(5):525-33. doi: 10.1080/15257770802089009.

Abstract

The synthesis of model 7 deazapurine derivatives related to tubercidin and toyocamycin has been performed. Tubercidin derivatives were obtained by simple conversion of the amino group of the heterocyclic moiety of the starting 7-deazadenosine compounds, into a hydroxyl group. Preparation of toyocamycin derivatives was accomplished by treatment of the silylated 6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-4-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-d-ribofuranose. The glycosylation reaction afforded a mixture of 8-bromo 7-cyano 2',3',5' tri-O-benzoyl 7-deazainosine and 6-bromo-5-cyano-3-(2',3',5'-tri-O-benzoyl-beta-d-ribofuranosyl)pyrrolo[2,3-d]-pyrimidin-4-one isomers: The structures were assigned on the basis of NMR spectroscopy studies. Next deprotection treatment gave the novel 7-deazainosine ribonucleosides.

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Drug Design
  • Inosine / analogs & derivatives*
  • Inosine / chemical synthesis
  • Inosine / chemistry
  • Inosine / pharmacology
  • Magnetic Resonance Spectroscopy
  • Pyrimidine Nucleosides / chemical synthesis*
  • Pyrimidine Nucleosides / chemistry
  • Pyrimidine Nucleosides / pharmacology
  • RNA Viruses / drug effects
  • RNA Viruses / physiology
  • Toyocamycin / analogs & derivatives
  • Toyocamycin / chemical synthesis
  • Toyocamycin / chemistry
  • Tubercidin / analogs & derivatives
  • Tubercidin / chemical synthesis
  • Tubercidin / chemistry
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Pyrimidine Nucleosides
  • Inosine
  • 7-deazainosine
  • Toyocamycin
  • Tubercidin