European Journal of Chemistry

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



Main Article Content

Tatiana Besset
Emmanuelle Braud
Rafika Jarray
Christiane Garbay
Stephanie Kolb
Pierre-Marc Leo
Christophe Morin

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


icon graph This Abstract was viewed 2242 times | icon graph Article PDF downloaded 701 times

How to Cite
(1)
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.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Nilsson, I.; Hoffman, I. Prog. Cell Cycle Res. 2000, 4, 107-114.
http://dx.doi.org/10.1007/978-1-4615-4253-7_10
PMid:10740819

[2]. Iliakis, G.; Wang, Y.; Guan, J.; Wang, H. Oncogene 2003, 22, 5834-5847.
http://dx.doi.org/10.1038/sj.onc.1206682
PMid:12947390

[3]. Karlsson-Rosenthal, C.; Millar, J. B. Trends Cell Biol. 2006, 16, 285-292.
http://dx.doi.org/10.1016/j.tcb.2006.04.002
PMid:16682204

[4]. Kristjansdottir, K.; Rudolph, J. Chem. Biol. 2004, 11, 1043-1051.
http://dx.doi.org/10.1016/j.chembiol.2004.07.007

[5]. Boutros, R.; Dozier, C.; Ducommun B. Curr. Opin. Cell Biol. 2006, 18, 185-191.
http://dx.doi.org/10.1016/j.ceb.2006.02.003
PMid:16488126

[6]. Galaktionov, K.; Chen, X.; Beach, D. Nature 1996, 382, 511-517.
http://dx.doi.org/10.1038/382511a0
PMid:8700224

[7]. Contour-Galcera, M. O.; Sidhu, A.; Prévost, G.; Bigg, D.; Ducommun, B. Pharmacol. Ther. 2007, 115, 1-12.
http://dx.doi.org/10.1016/j.pharmthera.2007.03.009

[8]. Nishikawa, Y.; Carr, B. I.; Wang, M.; Kar, S.; Finn, F.; Dowd, P.; Zheng, Z. B.; Kerns, J.; Naganathan, S. J. Biol. Chem. 1995, 270, 28304-28310.
http://dx.doi.org/10.1074/jbc.270.47.28304
PMid:7499329

[9]. Tamura, K.; Southwick, E. C.; Kerns, J.; Rosi, K.; Carr, B. I.; Wilcox, C.; Lazo, J. S. Cancer Res. 2000, 60, 1317-1325.
PMid:10728693

[10]. Garuti, L.; Roberti, M.; Pizzirani, D. Curr. Med. Chem. 2008, 15, 573-580.
http://dx.doi.org/10.2174/092986708783769722
PMid:18336271

[11]. Lazo, J. S.; Aslan, D. C.; Southwick, E. C.; Cooley, K. A.; Ducruet, A. P.; Joo, B.; Vogt, A.; Wipf P. J. Med. Chem. 2001, 44, 4042-4049.
http://dx.doi.org/10.1021/jm0102046
PMid:11708908

[12]. Lazo, J. S.; Nemoto, K.; Pestell, K. E.; Cooley, K.; Southwick, E. C.; Mitchell, D. A.; Furey, W.; Gussio, R.; Zaharevitz, D. W.; Joo, B.; Wipf, P. Mol. Pharmacol. 2002, 61, 720-728.
http://dx.doi.org/10.1124/mol.61.4.720
PMid:11901209

[13]. Pu, L.; Amoscato, A. A.; Bier, M. E.; Lazo, J. S. J. Biol. Chem. 2002, 277, 46877-46885.
http://dx.doi.org/10.1074/jbc.M207902200
PMid:12356752

[14]. Brisson, M.; Nguyen, T.; Wipf, P.; Joo, B.; Day, B. W.; Skoko, J. S.; Schreiber, E. M.; Foster, C.; Bansal, P.; Lazo, J. S. Mol. Pharmacol. 2005, 68, 1810-1820.
PMid:16155209

[15]. Cossy, J.; Belotti, D.; Brisson, M.; Skoko, J. J.; Wipf, P.; Lazo, J. S. Bioorg. Med. Chem. 2006, 14, 6283-6287.
http://dx.doi.org/10.1016/j.bmc.2006.05.053

[16]. Keinan, S.; Paquette, W. D.; Skoko, J. J.; Beratan, D. N.; Yang, W.; Shinde, S.; Johnston, P. A.; Lazo, J. S.; Wipf, P. Org. Biomol. Chem. 2008, 6, 3256-3263.
http://dx.doi.org/10.1039/b806712k

[17]. Braud, E.; Goddard, M. L.; Kolb, S.; Brun, M. P.; Mondesert, O.; Quaranta, M.; Gresh, N.; Ducommun, B.; Garbay, C. Bioorg. Med. Chem. 2008, 16, 9040-9049.
http://dx.doi.org/10.1016/j.bmc.2008.08.009

[18]. Brisson, M.; Foster, C.; Wipf, P.; Joo, B.; Tomko Jr, R. J.; Nguyen, T.; Lazo, J. S. Mol. Pharmacol. 2007, 71, 184-192.
http://dx.doi.org/10.1124/mol.106.028589
PMid:17018577

[19]. Lavergne, O.; Fernandes, A. C.; Brehu, L.; Sidhu, A.; Brezak, M. C.; Prévost, G.; Ducommun, B.; Contour-Calcera, M. O. Bioorg. Med. Chem. Lett. 2006, 16, 171-175.
http://dx.doi.org/10.1016/j.bmcl.2005.09.030

[20]. Brezak, M. C.; Valette, A.; Quaranta, M.; Contour-Galcera, M. O.; Jullien, D.; Lavergne, O.; Frongia, C.; Bigg, D.; Kasprzyk, P. G.; Prevost, G. P.; Ducommun, B. Int. J. Cancer 2009, 124, 1449-1456.
http://dx.doi.org/10.1002/ijc.24080
PMid:19065668

[21]. Brun, M. P.; Braud, E.; Angotti, D.; Mondésert, O.; Quaranta, M.; Montes, M.; Miteva, M.; Gresh, N.; Ducommun, B.; Garbay, C. Bioorg. Med. Chem. 2005, 13, 4871-4879.
http://dx.doi.org/10.1016/j.bmc.2005.05.005

[22]. Brezak, M. C.; Quaranta, M.; Mondésert, O.; Galcera, M. O.; Lavergne, O.; Alby, F.; Cazales, M.; Baldin, V.; Thurieau, C.; Harnett, J.; Lanco, C.; Kasprzyk, P. G.; Prévost, G. P.; Ducommun, B. Cancer Res. 2004, 64, 3320-3325.
http://dx.doi.org/10.1158/0008-5472.CAN-03-3984
PMid:15126376

[23]. Shi, S.; Katz, T. J.; Yang, B. V.; Liu, L. J. Org. Chem. 1995, 60, 1285-1297.
http://dx.doi.org/10.1021/jo00110a036

[24]. Shaikh, I. A.; Johnson, F.; Grollman, A. P. J. Med. Chem. 1986, 29, 1329-1340.
http://dx.doi.org/10.1021/jm00158a002
PMid:3525839

[25]. Crabbe, P.; Villarino, A.; Muchowski, J. M. J. Chem. Soc., Perkin Trans 1 1973, 2220-2222.

[26]. Saito, H.; Hirata, T.; Kasai, M.; Fujimoto, K.; Ashizawa, T.; Morimoto, M.; Sato, A. J. Med. Chem. 1991, 34, 1959-1966.
http://dx.doi.org/10.1021/jm00111a006
PMid:2066968

[27]. Xu, J. Z.; Chen, C. J. Labelled Compd. Radiopharm. 2006, 49, 1187-1200.
http://dx.doi.org/10.1002/jlcr.1139

[28]. Cherif, M.; Cotelle, P.; Catteau, J. P. Heterocycles 1992, 34, 1749-1758.
http://dx.doi.org/10.3987/COM-92-6070

[29]. Could, S. J.; Shen, B.; Whittle, Y. G. J. Am. Chem. Soc. 1989, 111, 7932-7938.
http://dx.doi.org/10.1021/ja00202a039

[30]. Lyon, M. A.; Lawrence, S.; Williams, D. J.; Jackson, Y. A. J. Chem. Soc., Perkin Trans 1 1999, 437-442.

[31]. Fries, K.; Reitz, H. Liebigs Ann. 1937, 527, 38-60.
http://dx.doi.org/10.1002/jlac.19375270103

[32]. Kitahara, Y.; Nakahara, S.; Tanaka, Y.; Kubo, A. Heterocycles 1992, 34, 1623-1630.
http://dx.doi.org/10.3987/COM-92-6102

[33]. Muchowski, J. M.; Maddox, M. L.; J. Mex. Chem. Soc. 2005, 49, 24-31.

[34]. Potts, K. T.; Bhattacharjee, D.; Walsh, E. B. J. Org. Chem. 1986, 51, 2011-2021.
http://dx.doi.org/10.1021/jo00361a014

[35]. Besset, T.; Morin, C. Synthesis 2009, 1753-1756.

[36]. Morin, C.; Besset, T.; Moutet, J. C.; Fayolle, M.; Brückner, M.; Limosin, D.; Becker, K.; Davioud-Charvet, E. Org. Biomol. Chem. 2008, 6, 2731-2742.
http://dx.doi.org/10.1039/b802649c

[37]. Showalter, H. D. H.; Pohlmann, G. Org. Prep. Proc. Int. 1992, 24, 484-487.
http://dx.doi.org/10.1080/00304949209356232

[38]. Legentil, L.; Bastide, J.; Delfourne, E. Tetrahedron Lett. 2003, 44, 2473-2475.
http://dx.doi.org/10.1016/S0040-4039(03)00320-4

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).