Synthesis and anti-tubulin activity of a 3'-(4-azidophenyl)-3'-dephenylpaclitaxel photoaffinity probe.
J Med Chem
; 47(26): 6459-65, 2004 Dec 16.
Article
em En
| MEDLINE
| ID: mdl-15588080
ABSTRACT
The synthesis and biological evaluation of a novel paclitaxel photoaffinity probe is described. The synthesis involved the preparation of an azide-containing C13 side chain through a Staudinger cycloaddition followed by a lipase-mediated kinetic resolution to obtain the azetidinone in 99% ee. Coupling of the enantiopure side chain precursor to 7-TES-baccatin III and subsequent silyl ether deprotection afforded 3'-(4-azidophenyl)-3'-dephenylpaclitaxel, which was shown to be as active as paclitaxel in tubulin assembly and cytotoxicity assays.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Azidas
/
Paclitaxel
/
Marcadores de Fotoafinidade
/
Moduladores de Tubulina
/
Antineoplásicos
Idioma:
En
Revista:
J Med Chem
Assunto da revista:
QUIMICA
Ano de publicação:
2004
Tipo de documento:
Article
País de afiliação:
Estados Unidos