European Journal of Chemistry 2011, 2(3), 365-371. doi:10.5155/eurjchem.2.3.365-371.289

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


Mohammed Shabaan (1) , Azza Taher Taher (2,*) , Eman Omar Osman (3)

(1) Department of Organic Chemistry, Faculty of Pharmacy, Cairo University, Cairo, 11562, Egypt
(2) Department of Organic Chemistry, Faculty of Pharmacy, Cairo University, Cairo, 11562, Egypt
(3) Department of Organic Chemistry, Faculty of Pharmacy, Cairo University, Cairo, 11562, Egypt
(*) Corresponding Author

Received: 27 Sep 2010, Accepted: 24 Dec 2010, Published: 30 Sep 2011

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


Keywords


Quinoxaline; 3,4-dihydroquinoxalin; Antimicrobial activity; CK1 inhibitors; CDK5 inhibitors; GSK-3β inhibitors

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.2.3.365-371.289

Article Metrics


This Abstract was viewed 850 times | PDF Article downloaded 543 times

Citations

/


[1]. Asmaa S. Salman, Naema A. Mahmoud, Anhar Abdel-Aziem, Mona A. Mohamed, Doaa M. Elsisi
Synthesis, Reactions and Antimicrobial Activity of Some New 3-Substituted Indole Derivatives
International Journal of Organic Chemistry  05(02), 81, 2015
DOI: 10.4236/ijoc.2015.52010
/


[2]. Azza Taher Taher, Nadia Abdalla Khalil, Eman Mohamed Ahmed, Yasser Mohamed Ragab
Synthesis of Certain 2-Substituted-1H-benzimidazole Derivatives as Antimicrobial and Cytotoxic Agents
Chemical and Pharmaceutical Bulletin  60(6), 778, 2012
DOI: 10.1248/cpb.60.778
/


[3]. Asmaa S. Salman, Anhar Abdel-Aziem, Marwa J. S. Alkubbat
Synthesis, Spectroscopic Characterization and Antimicrobial Activity of Some New 2-Substituted Imidazole Derivatives
International Journal of Organic Chemistry  05(01), 15, 2015
DOI: 10.4236/ijoc.2015.51003
/


[4]. Kapil Mohan Saini, Sonu Kumar, Monika Patel, Rakesh K. Saunthwal, Akhilesh K. Verma
Trifluoroacetic Acid Mediated One-Pot Synthesis of Furo-Fused Quinoxalines/Pyrazines
European Journal of Organic Chemistry  2017(25), 3707, 2017
DOI: 10.1002/ejoc.201700541
/


[5]. Lamia W. Mohamed, Azza T. Taher, Ghada S. Rady, Mamdouh M. Ali, Abeer E. Mahmoud
Synthesis and cytotoxic activity of certain benzothiazole derivatives against human MCF-7 cancer cell line
Chemical Biology & Drug Design  89(4), 566, 2017
DOI: 10.1111/cbdd.12879
/


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.


How to cite


Shabaan, M.; Taher, A.; Osman, E. Eur. J. Chem. 2011, 2(3), 365-371. doi:10.5155/eurjchem.2.3.365-371.289
Shabaan, M.; Taher, A.; Osman, E. Synthesis of novel 3,4-dihydroquinoxalin-2(1H)-one derivatives. Eur. J. Chem. 2011, 2(3), 365-371. doi:10.5155/eurjchem.2.3.365-371.289
Shabaan, M., Taher, A., & Osman, E. (2011). Synthesis of novel 3,4-dihydroquinoxalin-2(1H)-one derivatives. European Journal of Chemistry, 2(3), 365-371. doi:10.5155/eurjchem.2.3.365-371.289
Shabaan, Mohammed, Azza Taher Taher, & Eman Omar Osman. "Synthesis of novel 3,4-dihydroquinoxalin-2(1H)-one derivatives." European Journal of Chemistry [Online], 2.3 (2011): 365-371. Web. 23 Oct. 2019
Shabaan, Mohammed, Taher, Azza, AND Osman, Eman. "Synthesis of novel 3,4-dihydroquinoxalin-2(1H)-one derivatives" European Journal of Chemistry [Online], Volume 2 Number 3 (30 September 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.3.365-371.289

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.