7-deazainosine derivatives: synthesis and characterization of 7- and 7,8-substituted pyrrolo [2,3-d]pyrimidine ribonucleosides.
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.
Department of Pharmaceutical Sciences, University of Ferrara, Ferrara, Italy.
Nunzia
N
Ciliberti
Elisa
E
Durini
Stefano
S
Manfredini
Silvia
S
Vertuani
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D007288:Inosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D012328:RNA Viruses / Q000187:drug effects / Q000502:physiology; D014127:Toyocamycin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D014372:Tubercidin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D014779:Virus Replication / Q000187:drug effects
D000998:Antiviral Agents; D011741:Pyrimidine Nucleosides; D007288:Inosine; C049047:7-deazainosine; D014127:Toyocamycin; D014372:Tubercidin