1. 7-Deazainosine Derivatives: Synthesis and Characterization of 7- and 7,8-Substituted Pyrrolo [2,3-d]Pyrimidine Ribonucleosides
- Author
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Nunzia Ciliberti, Silvia Vertuani, Stefano Manfredini, and Elisa Durini
- Subjects
Magnetic Resonance Spectroscopy ,Glycosylation ,Pyrimidine ,Stereochemistry ,7-Deazainosine derivatives ,Virus Replication ,Antiviral Agents ,Biochemistry ,Tubercidin ,Synthesis ,chemistry.chemical_compound ,Genetics ,RNA Viruses ,Moiety ,Toyocamycin ,RNA viruses ,General Medicine ,Nuclear magnetic resonance spectroscopy ,Pyrimidine Nucleosides ,Inosine ,chemistry ,Drug Design ,Molecular Medicine ,7-deazainosine - 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.
- Published
- 2008
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