RSC Publishing


Publishing

 

Cover image for Dalton Transactions, select for current issue

Dalton Transactions

The international journal for inorganic, organometallic and bioinorganic chemistry



Subscribers

Non-subscribers

Free access



Paper

Dalton Trans., 2009, 10871 - 10881, DOI: 10.1039/b913570g

Synthesis, oxidation chemistry and cytotoxicity studies on ferrocene derivatives of diethylstilbestrol

Yong Leng Kelvin Tan, Pascal Pigeon, Elizabeth A. Hillard, Siden Top, Marie-Aude Plamont, Anne Vessières, Michael J. McGlinchey, Helge Müller-Bunz and Gérard Jaouen

A series of compounds is described in which one of the ethyl groups in diethylstilbestrol has been replaced by a ferrocenyl substituent. Only those derivatives incorporating phenol moieties underwent isomerisation from the Z to the E form, and some of them could be chemically oxidized to a quinone species. The compounds were less cytotoxic against hormone-independent MDA-MB-231 breast cancer cell lines than their corresponding ferrocenyl phenyl or phenol isomers in which the ferrocene and ethyl moieties are linked to the same carbon atom. The biochemical results were evaluated in conjunction with information obtained from electrochemical and chemical oxidation experiments.

Graphical abstract image for this article (ID: b913570g)