European Journal of Chemistry

Synthesis of novel 3,4-dihydroquinoxalin-2(1H)-one derivatives

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Published: Sep 30, 2011
DOI: https://doi.org/10.5155/eurjchem.2.3.365-371.289
Keywords:
Quinoxaline, 3, 4-dihydroquinoxalin, Antimicrobial activity, CK1 inhibitors, CDK5 inhibitors, GSK-3β inhibitors
Section
Research Article
Issue
Vol. 2 No. 3 (2011): September 2011
Dates
Received 2010-09-27
Accepted 2010-12-24
Published 2011-09-30


Main Article Content

Mohammed Shabaan
Department of Organic Chemistry, Faculty of Pharmacy, Cairo University, Cairo, 11562, Egypt
Azza Taher Taher
Department of Organic Chemistry, Faculty of Pharmacy, Cairo University, Cairo, 11562, Egypt
Eman Omar Osman
Department of Organic Chemistry, Faculty of Pharmacy, Cairo University, Cairo, 11562, Egypt

Abstract

New derivatives of 3,4-dihydroquinoxaline-2(1H)-one were synthesized and characterized. Representative examples were evaluated for their antimicrobial and antifungal activities using Tetracycline and Nystatin as reference compound. One of the tested compounds 10a was found to exhibit slight activity against Staphylococcus aureus. Compounds 10b, 11b and 14b showed slight activity against Escherichia coli. Moreover, nineteen compounds were screened for their inhibition effect on CDK5, CK1, and GSK-3β. None of the tested compounds showed an inhibition activity below 10 µM concentration.

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Shabaan, M.; Taher, A. T.; Osman, E. O. Synthesis of Novel 3,4-Dihydroquinoxalin-2(1H)-One Derivatives. Eur. J. Chem. 2011, 2, 365-371.

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References

[1]. Singh, S. K.; Saibaba, V.; Ravikumar, V.; Rudrawar, S. V.; Daga, P.; Rao, C. S.; Akhila, V.; Hegde, P.; Rao, Y. K. Bioorg. Med. Chem. 2004, 12, 1881-1893.
http://dx.doi.org/10.1016/j.bmc.2004.01.033

[2]. Burguete, A.; Pontiki, E.; Hadjipavlou-Litina, D.; Villar, R.; Vicente, E.; Solano, B.; Ancizu, S.; Perez-Silanes, S.; Aldana, I.; Monge, A. Bioorg. Med. Chem. Lett. 2007, 17, 6439-6443.
http://dx.doi.org/10.1016/j.bmcl.2007.10.002

[3]. Carta, A.; Loriga, M.; Paglitti, G.; Mattana, A.; Fiori, P.; Mollicotti, P.; Sechi, L.; Zanetti, S. Eur. J. Med. Chem. 2004, 39, 195-203.
http://dx.doi.org/10.1016/j.ejmech.2003.11.008
PMid:14987828

[4]. Jaso, A.; Zarranz, B.; Aldana, I.; Monge, A. J. Med. Chem. 2005, 48, 2019-2025.
http://dx.doi.org/10.1021/jm049952w
PMid:15771444

[5]. Badran, M.; Moneer, A.; Refaat, H. M.; El-Malah, A. J. Chinese Chem. Soc. 2007, 54, 469-478.

[6]. Badran, M.; Abouzid, K.; Hussein, M. H. Arch. Pharm. Res. 2003, 26, 107-113.
http://dx.doi.org/10.1007/BF02976653
PMid:12643584

[7]. Grande, F.; Aiello, F.; De Grazia, O.; Brizzi, A.; Garofalo, A.; Neamati, N. Bioorg. Med. Chem. 2007, 15, 288-294.
http://dx.doi.org/10.1016/j.bmc.2006.09.073

[8]. Moarbess, G.; Deleuze-Masquefa, C.; Bonnard, V.; Gayraud-Paniagua, S.; Vidal, J.; Bressolle, F.; Pinguet. F.; Bonnet, P. Bioorg. Med. Chem. 2008, 16, 6601-6610.
http://dx.doi.org/10.1016/j.bmc.2008.05.022

[9]. Vicente, E.; Ma, L.; Bongard, E.; Charnaud, S.; Villar, R.; Solano, B.; Burguete, A.; Perez-Silanes, S.; Aldana, I.; Vivas, L.; Monge, A. Eur. J. Med. Chem. 2008, 43, 1903-1910.
http://dx.doi.org/10.1016/j.ejmech.2007.11.024
PMid:18215443

[10]. Mahesh, R.; Devadoss, T.; Pandey, D. K.; Bahatt, S.; Yadav, S. K. Bioorg. Med. Chem. Lett. 2010, 20, 6773-6776.
http://dx.doi.org/10.1016/j.bmcl.2010.08.128

[11]. Chu-Moyer, M.; Ballinger, W.; Beebe, D.; Berger, R.; Coutcher, J.; Day, W.; Li, J.; Mylari, B.; Oates, P.; Weekly, M. J. Med. Chem. 2002, 45, 511-528.
http://dx.doi.org/10.1021/jm010440g
PMid:11784155

[12]. Dhavan, R.; Tsai, L. H. Nat. Rev. Mol. Cell Biol. 2001, 2, 749-759.
http://dx.doi.org/10.1038/35096019
PMid:11584302

[13]. Smith, S.; Tsai, L. H. Trends Cell Biol. 2003, 12(1), 28-35.
http://dx.doi.org/10.1016/S0962-8924(01)02181-X

[14]. Nikolic, M.; Dudek, H.; Kwon, Y. T.; Ramos, Y. F.; Tsai, L. H. Genes Dev. 1996, 10, 816-825.
http://dx.doi.org/10.1101/gad.10.7.816

[15]. Kwon, Y. T.; Gupta, A.; Zhou, Y.; Mikolic, M.; Tsai, L. H. Curr. Biol. 2000, 10, 363-372.
http://dx.doi.org/10.1016/S0960-9822(00)00411-5

[16]. Kwon, Y. T.; Tsai, L. H.; Crandell, J. E. J. Comp. Neurol. 1999, 415, 218-229.
http://dx.doi.org/10.1002/(SICI)1096-9861(19991213)415:2<218::AID-CNE6>3.0.CO;2-F

[17]. Tsai, L. H.; Lee, M. S.; Cruz, J. Biochim. Biophys. Acta 2004, 1697, 137-142.

[18]. Smith, P. D.; Crocker, S. J.; Jackson-Lewis, V.; Jordan-Sciutto, K. L.; Hayley, S.; Mount, M. P. O'Hare, M. J.; Callaaghan, S.; Slack, R. S.; Przedborski, S. Proc. Natl. Acad. Sci. 2003, 100, 13650-13655.
http://dx.doi.org/10.1073/pnas.2232515100
PMid:14595022 PMCid:263868

[19]. Patzke, H.; Tsai, L. H. Trends Neurosci. 2002, 25, 8-10.
http://dx.doi.org/10.1016/S0166-2236(00)02000-2

[20]. Wang, J.; Lui, S.; Fu, Y.; Wang, J. H.; Lu, Y. Nat. Neurosci. 2003, 6, 1039-1047.
http://dx.doi.org/10.1038/nn1119
PMid:14502288

[21]. Rzasa, R. M.; Kaller, M.; Liu, G.; Magal, E.; Nguyen, T.; Osslund, D.; Powers, D.; Santora, V. J.; Wang, H. L.; Xiaoling Xiong, X.; Zhong, W.; Norman, M. H. Bioorg. Med. Chem. 2007, 15, 6574-6595.
http://dx.doi.org/10.1016/j.bmc.2007.07.005

[22]. Zhong, W.; Liu, H.; Kaller, M.; Henley, C.; Magal, E.; Nguyen, T.; Osslund, T. D.; Powers, D.; Wang, H. L.; Xiaoling, X.; Norman, M. H. Bioorg. Med. Chem. Lett. 2007, 17, 5384-5389.
http://dx.doi.org/10.1016/j.bmcl.2007.07.045

[23]. Fatutta, S.; Stener, A. Gazz. Chim. Ital. 1958, 88, 89-100.

[24]. Freri, M. Gazz. Chim. Ital. 1938, 68, 612-619.

[25]. Mokhtar, H. J. Chem. Soc. Pak. 1988, 10, 414-420.

[26]. Rashed, N.; El-Masry, A.; El-Ashry, E.; Amer, A.; Zimmer, H. J. Heterocyclic Chem. 1990, 27, 691-693.
http://dx.doi.org/10.1002/jhet.5570270339

[27]. Meijer, L.; Thunnissen, A.; White, A. W.; Garnier, M.; Nikolic, M.; Tsai, L. H.; Walter, J.; Cleverley, K. E.; Salinas, P. C.; Wu, Y. Z.; Biernat, J.; Mandelkow, E. M.; Pettit, Kim, S. H.; G. R. Chemistry & Biology 2000, 7(1), 51-63.
http://dx.doi.org/10.1016/S1074-5521(00)00063-6

[28]. Meijer, L.; Moulinoux, J. P. Eur. J. Biochem. 1997, 243, 527-536.
http://dx.doi.org/10.1111/j.1432-1033.1997.t01-2-00527.x
PMid:9030781

[29]. Borgne, A.; Ostvoid, A. C.; Flament, S.; Meijer, L. J. Biol. Chem. 1999, 274, 11977-11986.
http://dx.doi.org/10.1074/jbc.274.17.11977
PMid:10207019

[30]. Machacek, V.; Toman, J.; Klicnar, J. Coll. Czech. Chem. Commun. 1978, 43, 1634-1638.

[31]. Noyce, D. S.; Pryor, W. A.; Bottini, A. H. J. Am. Chem. Soc. 1955, 77, 1402-1405.
http://dx.doi.org/10.1021/ja01611a002

[32]. Katritzky, A. R.; Yousaf, T. I.; Ostercamp, D. L. Tetrahedron, 1986, 42, 5729-5738.
http://dx.doi.org/10.1016/S0040-4020(01)88178-3

[33]. Bahulayan, D.; Sukumar, R.; Sabu, K. R.; Lalithambika, M. Green Chem. 1999, 1, 191-193.
http://dx.doi.org/10.1039/a906165g

[34]. Kalsi, P. S. Spectroscopy of organic compounds, New Age International (P) Ltd., 5th Edition, 2002, pp.178.

[35]. Gökhan, N.; YeÅilada, A.; Uçar, G.; Erol, K.; Bilgin, A. A. Arch. Pharm. 2003, 336, 362-371.

[36]. Kandeel, M.; Omar, A. H. Bull. Fac. Pharm. Cairo Univ. 2003, 41, 43-50.

[37]. Shawali, A.; Fahmi, A. Ind. J. Chem. 1975, 13, 105-109.

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