Synthèse de composés organométalliques de la série du ferrocénophane et évaluation de leurs activités antiprolifératives sur les cellules du cancer du sein et de la prostate

Abstract : The development of organometallic compounds for cancer therapeutics is one of the most quickly growing areas of bioorganometallic chemistry. Among organometallic compounds based on endocrine modulators, the most active and well-studied are the ferrocenyl derivatives of tamoxifen, developed by the Jaouen group. Ferrocifen and ferrociphenol are very active against both hormone dependent (MCF-7) and hormone independent (MDA-MB-231) breast cancer cells. Ferrocenophanyl diphenol, an analogue of ferrociphenol, has been found much more active than this latter compound. The objective of the present work is to study the synthesis and the antitumor activity of ferrocenophane series. Most of new compounds that were prepared are 1-(diarylmethylidene)-[3]ferrocenophanes bearing one or two substituents (R1, R2 = H, OH, OAc, NH2, NHAc, Br, CN, NHCO(CH2)2NMe2, O(CH2)3NMe2 or O(CH2)2COOEt) on the para position of the aryl group. These compounds confirm the high antitumor activity of the ferrocenophane series compared to the ferrocene series. Pinacols and pinacolic rearrangement compounds were studied; they were obtained from a McMurry coupling reaction. Pinacols showed high antitumor activity against MDA-MB-231 cells while the pinacolic rearrangement compounds are less active. This work shows clearly that the ferrocenophane series is more active than the ferrocene series against hormone-independent breast cancer cells.


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Submitted on : Wednesday, June 15, 2011 - 11:00:33 AM
Last modification on : Wednesday, June 15, 2011 - 4:06:53 PM

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  • HAL Id : pastel-00600598, version 1

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Meral Görmen. Synthèse de composés organométalliques de la série du ferrocénophane et évaluation de leurs activités antiprolifératives sur les cellules du cancer du sein et de la prostate. Cancer. Chimie ParisTech, 2010. French. <pastel-00600598>

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