European Journal of Chemistry

Preparation and evaluation of a set of bis(methoxycarbonylmethylthio) heteroquinones as CDC25B phosphatase inhibitors

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Published: Dec 31, 2011
DOI: https://doi.org/10.5155/eurjchem.2.4.433-440.400
Keywords:
Heterocyclic quinones, CDC25B inhibitors, Enzymatic activity, Phosphatase, Cancer, Cell cycle
Section
Research Article
Issue
Vol. 2 No. 4 (2011): December 2011
Dates
Received 2011-02-03
Accepted 2011-03-29
Published 2011-12-31


Main Article Content

Tatiana Besset
Departement de Chimie Moleculaire (CNRS, UMR 5250, ICMG FR-2607), Universite Joseph Fourier, 301 Rue de la chimie, F-38402 Grenoble Cedex, France
Emmanuelle Braud
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, 45 Rue des Saints Peres, F-75006 Paris, France
Rafika Jarray
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, 45 Rue des Saints Peres, F-75006 Paris, France
Christiane Garbay
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, 45 Rue des Saints Peres, F-75006 Paris, France
Stephanie Kolb
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, 45 Rue des Saints Peres, F-75006 Paris, France
Pierre-Marc Leo
Departement de Chimie Moleculaire (CNRS, UMR 5250, ICMG FR-2607), Universite Joseph Fourier, 301 Rue de la chimie, F-38402 Grenoble Cedex, France
Christophe Morin
Departement de Chimie Moleculaire (CNRS, UMR 5250, ICMG FR-2607), Universite Joseph Fourier, 301 Rue de la chimie, F-38402 Grenoble Cedex, France

Abstract

A set of new heteroquinone derivatives bearing two methoxycarbonylmethylthio groups on the benzoquinone ring were synthesized and evaluated for CDC25B phosphatase inhibitory activity. All compounds inhibited the enzyme with IC50 values in the micromolar range regardless of the size and heteroatoms constituting the heterocycle fused to the quinone ring. Moreover, these quinonoid-based compounds showed moderate antiproliferative activity toward two cancer cell lines (HeLa and MiaPaca-2). These results provide additional data for CDC25 inhibition by quinone-type derivatives and highlight the importance of substituents on the quinonic moiety.

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Besset, T.; Braud, E.; Jarray, R.; Garbay, C.; Kolb, S.; Leo, P.-M.; Morin, C. Preparation and Evaluation of a Set of bis(methoxycarbonylmethylthio) Heteroquinones As CDC25B Phosphatase Inhibitors. Eur. J. Chem. 2011, 2, 433-440.

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