Issue 28, 2010
From the journal:

Chemical Communications

Synthesis of cytotoxic ferrocenyl flavones via a ferricenium-mediated 1,6-oxidative cyclization†

Jean-Philippe Monserrat,a   Guy G. Chabot,b   Louis Hamon,c   Lionel Quentin,b   Daniel Scherman,b   Gérard Jaouena  and  Elizabeth A. Hillard*a  

* Corresponding authors

a Chimie ParisTech (Ecole Nationale Supérieure de Chimie de Paris), Laboratoire Charles Friedel, UMR CNRS 7223, 11 rue Pierre et Marie Curie, 75231 Paris cedex 05, France
E-mail: elizabeth-hillard@chimie-paristech.fr
Fax: +33 1 43 25 79 75
Tel: +33 1 44 27 66 98

b Chimie ParisTech (Ecole Nationale Supérieure de Chimie de Paris), Département Friedel, Université Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, Laboratoire de Pharmacologie Chimique, Génétique et Imagerie (CNRS UMR 8151-INSERM U 1022), 4 avenue de l'Observatoire, 75006 Paris, France

c Institut Parisien de Chimie Moléculaire, UMR CNRS 7201, Université Pierre et Marie Curie, CC47, 4 Place Jussieu, 75252 Paris Cedex 05, France

Abstract

The oxidation of the ferrocenyl group of 2′-hydroxyferrocenyl chalcones activates the β-position of the unsaturated ketone to nucleophilic attack to yield the first examples of ferrocenyl flavones. These compounds are significantly more cytotoxic than their organic analogs on B16 melanoma cells, with IC50 values in the low micromolar range.

Graphical abstract: Synthesis of cytotoxic ferrocenyl flavones via a ferricenium-mediated 1,6-oxidative cyclization

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DOI
https://doi.org/10.1039/C0CC01290D
Article type
Communication
Submitted
07 May 2010
Accepted
21 May 2010
First published
16 Jun 2010

Chem. Commun., 2010,46, 5145-5147

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Synthesis of cytotoxic ferrocenyl flavones via a ferricenium-mediated 1,6-oxidative cyclization

J. Monserrat, G. G. Chabot, L. Hamon, L. Quentin, D. Scherman, G. Jaouen and E. A. Hillard, Chem. Commun., 2010, 46, 5145 DOI: 10.1039/C0CC01290D

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