European Journal of Chemistry

A convenient synthesis and preparation of the derivatives of ethyl-6-(8-hydroxyquinolin-5-yl)-3-methylpyridazine-4-carboxylate as antimicrobial agents



Main Article Content

Shawkat Ahmed Abdelmohsen

Abstract

Synthesis of ethyl 6-(8-hydroxyquinolin-5-yl)-3-methylpyridazin-4-carboxylate (4) via one-pot three component reaction of ethyl acetoacetate with (8-hydroxyquinolin-5-yl)(oxo) acetaldehyde (2) in the presence of hydrazine hydrate at room temperature in water was described. A new series of heterocyclic moieties such as oxadiazoles, triazoles, pyrazoles and Schiff bases were prepared and characterized. The structures of the newly synthesized compounds were established by elemental and spectral data. The antimicrobial activity of some of the synthesized compounds was examined against two Gram‐positive bacteria, two Gram‐negative bacteria and four fungi. The results showed that the tested compounds exhibited significant to moderate antimicrobial.


icon graph This Abstract was viewed 2061 times | icon graph Article PDF downloaded 1003 times

How to Cite
(1)
Abdelmohsen, S. A. A Convenient Synthesis and Preparation of the Derivatives of Ethyl-6-(8-Hydroxyquinolin-5-Yl)-3-Methylpyridazine-4-Carboxylate As Antimicrobial Agents. Eur. J. Chem. 2014, 5, 517-525.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Coelho, A.; Sotelo, E.; Novoa, H.; Peeters, O. M.; Blaton, N.; Ravina, E. Tetrahedron 2004, 45, 3459-3463.
http://dx.doi.org/10.1016/j.tetlet.2004.03.005

[2]. Nagawade, R. R.; Khanna, V. V.; Bhagwat, S. S.; Shinde, D. B. Eur. J. Med. Chem. 2005, 40, 1325-1330.
http://dx.doi.org/10.1016/j.ejmech.2005.05.012

[3]. Sotelo, E.; Ravina, E. Synthetic Commun. 2002, 32, 1675-1680.
http://dx.doi.org/10.1081/SCC-120004258

[4]. Tamayo, N.; Liao, L.; Goldberg, M.; Powers, D.; Tudor, Y. Y.; Yu, V.; Wong, L. M.; Henkle, B.; Middleton, S.; Syed, R.; Harvey, T.; Jang, G.; Hungate, R.; Dominguez, C. Bioorg. Med. Chem. Lett. 2005, 15, 2409-2413.
http://dx.doi.org/10.1016/j.bmcl.2005.02.010

[5]. Rohet, F.; Rubat, C.; Coudert, P.; Couquelet, J. Bioorgan. Med. Chem. 1997, 5, 655-659.
http://dx.doi.org/10.1016/S0968-0896(97)00006-0

[6]. Butnariu, R. M.; Caprosu, M. D.; Bejan, V.; Ungureanu, M.; Poiata, A.; Tuchilus, C.; Florescu, M.; Mangalagiu, I. I. J. Heterocyclic Chem. 2007, 44, 1149-1152.
http://dx.doi.org/10.1002/jhet.5570440528

[7]. Kandile, N. G.; Mohamed, M. I.; Zaky, H.; Mohamed, H. M. Eur. J. Med. Chem. 2009, 44, 1989-1996.
http://dx.doi.org/10.1016/j.ejmech.2008.09.047

[8]. Dogruer, D. S.; Sahin, M. F.; Kupeli, E.; Yesilada, E. Turk. J. Chem. 2003, 27, 727-738.

[9]. Caliskan, E. B.; Sukuroglu, M.; Coban, T.; Banoglu, E.; Suzen, S. J. Enzym. Inhib. Med. Ch. 2007, 23, 225-229.
http://dx.doi.org/10.1080/14756360701475167

[10]. Cherng, S. C.; Huang, W. H.; Shian, C. Y.; Lee, A. R.; Chou, T. C. Eur. J. Pharmacol. 2006, 532, 32-37.
http://dx.doi.org/10.1016/j.ejphar.2005.12.022

[11]. Malinka, W.; Redzica, A.; Lozach, O. II Farmaco 2004, 59, 457-462.
http://dx.doi.org/10.1016/j.farmac.2004.03.002

[12]. Asif, M. J. Adv. Sci. Res. 2010, 1, 35-45.

[13]. Cao, S.; Qian, X.; Song, G.; Chai, B.; Jiang, Z. J. Agr. Food Chem. 2003, 51, 152-155.
http://dx.doi.org/10.1021/jf0208029

[14]. Bansal, R.; Kumar, D.; Carron, R. Eur. J. Med. Chem. 2009, 44, 4441-4447.
http://dx.doi.org/10.1016/j.ejmech.2009.06.006

[15]. Rathish, I. G.; Javed, K.; Bano, S.; Ahmad, S.; Alam, M. S.; Pillai, K. K. Eur. J. Med. Chem. 2009, 44, 2673-2678.
http://dx.doi.org/10.1016/j.ejmech.2008.12.013

[16]. Naud, S.; Pipelier, M.; Viault, G.; Adjou, A.; Huet, F.; Legoupy, S.; Aubertin, A. M.; Evain, M.; Dubreuil, D. Eur. J. Org. Chem. 2007, 20, 3296-3310.
http://dx.doi.org/10.1002/ejoc.200700102

[17]. Orazio, A. A.; Gianfranco, F.; Paolino, F.; Francesca, R. P.; Stefania, S. Org. Lett. 2009, 11, 309-312.
http://dx.doi.org/10.1021/ol802432z

[18]. Abdel-Mohsen, Sh. A. B. Korean Chem. Soc. 2005, 26, 719-728.
http://dx.doi.org/10.5012/bkcs.2005.26.5.719

[19]. Abdel-Mohsen, Sh. A. Chinese. J. Chem. Soc. 2003, 50, 1085-1092.

[20]. Khalil, Z. H.; Yanni, A. S.; Khalaf, A. A.; Abdel-Hafez, A. A.; Abdou, R. F. B. Chem. Soc. Jpn. 1988, 61, 1345-1349.
http://dx.doi.org/10.1246/bcsj.61.1345

[21]. Khalil, Z. H.; Abdel-Hafez, A. A.; Geies, A. A.; El-Dean, A. M. K. B. Chem. Soc. Jpn. 1991, 64, 668-670.
http://dx.doi.org/10.1246/bcsj.64.668

[22]. Khalil, Z. H.; Yanni, A. S.; Gaber, A. M.; Abdel-Mohsen, Sh. A. Phosphorus Sulfur and Silicon 2000, 166, 57-61.
http://dx.doi.org/10.1080/10426500008076531

[23]. Khalafy, J.; Rimaz, M.; Ezzati, M. Curr. Chem. Lett. 2012, 1, 115-122.
http://dx.doi.org/10.5267/j.ccl.2012.6.001

[24]. Matsumura, K. J. Am. Chem. Soc. 1930, 52, 4433-4437.
http://dx.doi.org/10.1021/ja01374a037

[25]. Vishun Vats, R. K.; Prathibha, Sh. E-J Chem. 2010, 7, 1040-1044.

[26]. Abdel-Mohsen, Sh. A.; Abdel-Hafez, Sh. H.; Geies, A. A. Chinese J. Chem. Soc. 2006, 16, 909-914.

[27]. Cooper, R. E.; Kavanageh, F. W. Analytical Microbiology, Vol. I and II, Academic press: New York and London, 1972.

Supporting Agencies

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).