Design and racemic synthesis of conformationally restricted carbocyclic pyrimidine nucleoside analogs based on the structure of the L-nucleoside residue in heterochiral DNA.
Carbocyclic pyrimidine nucleoside analogs which have restricted glycosidic conformation at chi approximately 180 degrees were designed, based on the conformational features of the L-nucleotide residue in heterochiral DNA, and synthesized. The synthesis of (+/-)-carbocyclic 6,6'-O-cyclo-2'-deoxyuridine was achieved via bromination and subsequent intramolecular cyclization of carbocyclic 6'beta-hydroxy-2'-deoxyuridine. (+/-)-Carbocyclic 6,6'-O-cyclo-2'-deoxycytidine was synthesized from protected carbocyclic 6,6'-O-cyclo-2'-deoxyuridine via the 4-triazole intermediate.
Urata
H
H
Osaka University of Pharmaceutical Sciences, Takatsuki, Japan.
Miyagoshi
H
H
Kakuya
H
H
Tokumoto
H
H
Kawahata
T
T
Otake
T
T
Akagi
M
M
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000494:pharmacology; D002478:Cells, Cultured / Q000187:drug effects; D003562:Cytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D015195:Drug Design; D015497:HIV-1 / Q000187:drug effects; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
D019380:Anti-HIV Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D011741:Pyrimidine Nucleosides; C111700:carbocyclic 6,6'-O-cyclo-2'-deoxycytidine; D003562:Cytidine