Synthesis and cytotoxic evaluation of combretafurazans

Gian Cesare Tron, Francesca Pagliai, Erika Del Grosso, Armando A. Genazzani, Giovanni Sorba

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

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.

Lingua originaleInglese
pagine (da-a)3260-3268
Numero di pagine9
RivistaJournal of Medicinal Chemistry
Volume48
Numero di pubblicazione9
DOI
Stato di pubblicazionePubblicato - 5 mag 2005

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