3'-Carbon-substituted pyrimidine nucleosides having a 2',3'-dideoxy and 2',3'-didehydro-2',3'-dideoxy structure: synthesis and antiviral evaluation.
Antivir Chem Chemother
; 17(4): 225-34, 2006.
Article
em En
| MEDLINE
| ID: mdl-17066900
ABSTRACT
The bis(tributylstannyl) derivative of 2',3'-didehydro-2',3'-dideoxyuridine (d4U) underwent an anionic 5'-O-->3'-C stannyl migration to yield the 3'-tributylstannyl-d4U. This compound, with its vinylstannane structure, allowed ready access to the preparation of 3'-carbon-substituted analogues through the Stille reaction. A conventional transformation of the uracil moiety of these d4U analogues led to the corresponding 2',3'-didehydro-2',3'-dideoxycytidine (d4C) counterparts. Some 2',3'-dideoxycytidine (ddC) analogues were also synthesized. Antiviral evaluation revealed that none of these analogues showed activity against HIV, hepatitis B virus, herpes simplex virus-1 (HSV-1) and HSV-2.
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Base de dados:
MEDLINE
Assunto principal:
Antivirais
/
Nucleosídeos de Pirimidina
/
Didesoxinucleosídeos
/
Zalcitabina
/
Fármacos Anti-HIV
Idioma:
En
Ano de publicação:
2006
Tipo de documento:
Article