European Journal of Chemistry 2011, 2(4), 433-440 | doi: https://doi.org/10.5155/eurjchem.2.4.433-440.400 | Get rights and content




  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE

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


Tatiana Besset (1) , Emmanuelle Braud (2,*) , Rafika Jarray (3) , Christiane Garbay (4) , Stephanie Kolb (5) , Pierre-Marc Leo (6) , Christophe Morin (7)

(1) Departement de Chimie Moleculaire (CNRS, UMR 5250, ICMG FR-2607), Universite Joseph Fourier, 301 Rue de la chimie, F-38402 Grenoble Cedex, France
(2) Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, 45 Rue des Saints Peres, F-75006 Paris, France
(3) Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, 45 Rue des Saints Peres, F-75006 Paris, France
(4) Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, 45 Rue des Saints Peres, F-75006 Paris, France
(5) Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, CNRS UMR 8601, Université Paris Descartes, 45 Rue des Saints Peres, F-75006 Paris, France
(6) Departement de Chimie Moleculaire (CNRS, UMR 5250, ICMG FR-2607), Universite Joseph Fourier, 301 Rue de la chimie, F-38402 Grenoble Cedex, France
(7) Departement de Chimie Moleculaire (CNRS, UMR 5250, ICMG FR-2607), Universite Joseph Fourier, 301 Rue de la chimie, F-38402 Grenoble Cedex, France
(*) Corresponding Author

Received: 03 Feb 2011 | Accepted: 29 Mar 2011 | Published: 31 Dec 2011 | Issue Date: December 2011

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.

2_4_433_440_800


Keywords


Heterocyclic quinones; CDC25B inhibitors; Enzymatic activity; Phosphatase; Cancer; Cell cycle

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DOI: 10.5155/eurjchem.2.4.433-440.400

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[1]. I. V. Smolyaninov, O. V. Pitikova, A. I. Poddel’sky, N. T. Berberova
Electrochemical transformations and antiradical activity of asymmetrical RS-substituted pyrocatechols
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DOI: 10.1007/s11172-018-2299-9
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[2]. Ivan Smolyaninov, Olga Pitikova, Eugenia Korchagina, Andrey Poddel’sky, Svetlana Luzhnova, Nadezhda Berberova
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How to cite


Besset, T.; Braud, E.; Jarray, R.; Garbay, C.; Kolb, S.; Leo, P.; Morin, C. Eur. J. Chem. 2011, 2(4), 433-440. doi:10.5155/eurjchem.2.4.433-440.400
Besset, T.; Braud, E.; Jarray, R.; Garbay, C.; Kolb, S.; Leo, P.; Morin, C. Preparation and evaluation of a set of bis(methoxycarbonylmethylthio) heteroquinones as CDC25B phosphatase inhibitors. Eur. J. Chem. 2011, 2(4), 433-440. doi:10.5155/eurjchem.2.4.433-440.400
Besset, T., Braud, E., Jarray, R., Garbay, C., Kolb, S., Leo, P., & Morin, C. (2011). Preparation and evaluation of a set of bis(methoxycarbonylmethylthio) heteroquinones as CDC25B phosphatase inhibitors. European Journal of Chemistry, 2(4), 433-440. doi:10.5155/eurjchem.2.4.433-440.400
Besset, Tatiana, Emmanuelle Braud, Rafika Jarray, Christiane Garbay, Stephanie Kolb, Pierre-Marc Leo, & Christophe Morin. "Preparation and evaluation of a set of bis(methoxycarbonylmethylthio) heteroquinones as CDC25B phosphatase inhibitors." European Journal of Chemistry [Online], 2.4 (2011): 433-440. Web. 16 Dec. 2019
Besset, Tatiana, Braud, Emmanuelle, Jarray, Rafika, Garbay, Christiane, Kolb, Stephanie, Leo, Pierre-Marc, AND Morin, Christophe. "Preparation and evaluation of a set of bis(methoxycarbonylmethylthio) heteroquinones as CDC25B phosphatase inhibitors" European Journal of Chemistry [Online], Volume 2 Number 4 (31 December 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.4.433-440.400

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