European Journal of Chemistry 2014, 5(3), 517-525. doi:10.5155/eurjchem.5.3.517-525.1072

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


Shawkat Ahmed Abdelmohsen (1,*)

(1) Department of Chemistry, Faculty of Science, Assiut University, Assiut 71516, Egypt
(*) Corresponding Author

Received: 10 Apr 2014, Accepted: 06 Jun 2014, Published: 30 Sep 2014

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.


Keywords


Triazoles; Pyrazoles; Pyridazines; Oxadiazoles; One-pot reaction; Antimicrobial activity

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.5.3.517-525.1072

Article Metrics


This Abstract was viewed 654 times | PDF Article downloaded 333 times

Citations

/


[1]. A. V. Velikorodov, E. A. Shustova
Synthesis and some transformations of methyl [4-(oxoacetyl)phenyl]carbamate
Russian Journal of Organic Chemistry  53(1), 82, 2017
DOI: 10.1134/S1070428017010146
/


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.


How to cite


Abdelmohsen, S. Eur. J. Chem. 2014, 5(3), 517-525. doi:10.5155/eurjchem.5.3.517-525.1072
Abdelmohsen, S. 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(3), 517-525. doi:10.5155/eurjchem.5.3.517-525.1072
Abdelmohsen, S. (2014). A convenient synthesis and preparation of the derivatives of ethyl-6-(8-hydroxyquinolin-5-yl)-3-methylpyridazine-4-carboxylate as antimicrobial agents. European Journal of Chemistry, 5(3), 517-525. doi:10.5155/eurjchem.5.3.517-525.1072
Abdelmohsen, Shawkat. "A convenient synthesis and preparation of the derivatives of ethyl-6-(8-hydroxyquinolin-5-yl)-3-methylpyridazine-4-carboxylate as antimicrobial agents." European Journal of Chemistry [Online], 5.3 (2014): 517-525. Web. 19 Sep. 2019
Abdelmohsen, Shawkat. "A convenient synthesis and preparation of the derivatives of ethyl-6-(8-hydroxyquinolin-5-yl)-3-methylpyridazine-4-carboxylate as antimicrobial agents" European Journal of Chemistry [Online], Volume 5 Number 3 (30 September 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.3.517-525.1072

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.