European Journal of Chemistry

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



Main Article Content

Mohammed Shabaan
Azza Taher Taher
Eman Omar Osman

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.

2_3_365_371_800


icon graph This Abstract was viewed 1873 times | icon graph Article PDF downloaded 988 times

How to Cite
(1)
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.

Article Details

Share
Crossref - Scopus - Google - European PMC
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.

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).