Synthesis and cytotoxic evaluation of combretafurazans.
J Med Chem
; 48(9): 3260-8, 2005 May 05.
Article
en En
| MEDLINE
| ID: mdl-15857132
Combretastatin A-4 is an antitumoral and antitubulin agent that is active only in its cis configuration. In the present manuscript, we have synthesized cis-locked combretastatins embodying a furazan ring (combretafurazans). To achieve this, we have developed a new strategy that exploits the dehydration of vicinal dioximes using the Mitsunobu reaction. Among the advantages of following such a strategy are the mild conditions used for the construction of the diarylfurazan derivatives, allowing for the presence of highly functionalized substrates and deactivated aromatic rings. Combretafurazans are more potent in vitro cytotoxic compounds compared to combretastatins in neuroblastoma cells, yet maintaining similar structure-activity relationship and pharmacodynamic profiles.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Oxadiazoles
/
Derivados del Benceno
/
Antineoplásicos
Límite:
Humans
Idioma:
En
Revista:
J Med Chem
Asunto de la revista:
QUIMICA
Año:
2005
Tipo del documento:
Article
País de afiliación:
Italia
Pais de publicación:
Estados Unidos