Synthesis, antimicrobial activity and molecular modeling study of some new pyrimidine derivatives

Wasfi Abood Al-Masoudi; Abeer Laily Mohmmed; Wamedh Hashim Abass; Najim Aboud Al-Masoudi

doi:10.5155/eurjchem.6.2.127-130.1175

PDF

Published: Jun 30, 2015

DOI: https://doi.org/10.5155/eurjchem.6.2.127-130.1175

Keywords:

2D NMR, Antibiotics, Pyrimidine, Schiff’s bases, Antimicrobial activity, Molecular modeling study

Section

Research Article

Issue

Vol. 6 No. 2 (2015): June 2015

Dates

Received 2014-10-27
Accepted 2014-11-27
Published 2015-06-30

Wasfi Abood Al-Masoudi

Department of Physiology and Chemistry, College of Veterinary, University of Basrah, Basrah, 61001, Iraq

Abeer Laily Mohmmed

Department of Microbiology, College of Veterinary, University of Basrah, Basrah, 61001, Iraq

Wamedh Hashim Abass

Department of Public Health, College of Veterinary, University of Basrah, Basrah, 61001, Iraq

Najim Aboud Al-Masoudi

Department of Chemistry, College of Science, University of Basrah, Basrah, 61001, Iraq

Abstract

Condensation of 2-amino-4-chloro-6-methoxypyrimidine with aromatic aldehydes (2-hydroxy-1-naphthaldehyde, 3,4-dihydroxybenzaldehyde and piperonal) afforded products in good yields. The synthesized compounds (Schiff base of pyrimidine derivatives) were screened for their antibacterial activity against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Klebsille, Pseudomonas aeruginosa and Salmonella. Additionally, the compounds were tested for antifungicidal activity against Candida albicans, Candida tropicalis and Aspergillus fumigatus. All compounds exhibited potent antibacterial and antifungal activity. Molecular modeling studies were performed, showing the hydrogen bindings and hydrophobic interactions.

This Abstract was viewed 1740 times |

Article PDF downloaded 894 times

How to Cite

(1)

Al-Masoudi, W. A.; Mohmmed, A. L.; Abass, W. H.; Al-Masoudi, N. A. Synthesis, Antimicrobial Activity and Molecular Modeling Study of Some New Pyrimidine Derivatives. Eur. J. Chem. 2015, 6, 127-130.

Links for Article

Crossref - Scopus - Google - European PMC

References

[1]. Jain, K. S.; Chitre, T. S.; Miniyar, P. B.; Kathiravan, M. K.; Bendre, V. S.; Veer, V. S.; Shahane, S. R.; Shishoo, C. J. Curr. Sci. 2006, 90, 793-803.

[2]. Patel, D. H.; Mistry, B. D.; Desai, K. R. Indian J. Hetero. Chem. 2003, 13, 179‐180.

[3]. Bantawal, S. H.; Manjathuru, M.; Mari, K. S.; Padiyath, K. M. Bioorg. Med. Chem. 2006, 14, 2040‐2047.
http://dx.doi.org/10.1016/j.bmc.2005.10.053

[4]. Sharma, P.; Rane, N.; Gurram, V. K. Bioorg. Med. Chem. Lett. 2004, 14, 4185‐4190.
http://dx.doi.org/10.1016/j.bmcl.2004.06.014

[5]. Adnan, A. B.; Hesham, T. Z.; Sherif, A. F.; Azza, M. B. Eur. J. Med. Chem. 2003, 38, 27‐36.
http://dx.doi.org/10.1016/S0223-5234(02)00009-0

[6]. Russell, R. K.; Press, J. B.; Rampulla, R. A.; McNally, J. J.; Falotico, R.; Keiser, J. A. J. Med. Chem. 1988, 31, 1786‐1793.
http://dx.doi.org/10.1021/jm00117a019

[7]. Cocco, M. T.; Congiu, C.; Lilliu, V. Bioorg. Med. Chem. 2006, 14, 366‐372.
http://dx.doi.org/10.1016/j.bmc.2005.08.012

[8]. Heidelberger, C.; Chaudhuri, N. K.; Danneberg, P.; Mooren, D.; Griesbach, L.; Duschinsky, R.; Schnitzer, R. J.; Pleven, E.; Scheiner, J. Nature 1957, 179, 663‐666.
http://dx.doi.org/10.1038/179663a0

[9]. Beattie, J. F.; Breault, G. A.; Ellston, R. P. A.; Green, S.; Jewsbury, P. J.; Midgley, C. J.; Naven, R. T.; Minshull, C. A.; Pauptit, R. A.; Tucker, J. A.; Pease, J. E. Bioorg. Med. Chem. Lett. 2003, 13, 2955‐2960.
http://dx.doi.org/10.1016/S0960-894X(03)00202-6

[10]. Kimura, H.; Katoh, T.; Kajimoto, T.; Node, M.; Hisaki, M.; Sugimoto, Y.; Majima, T.; Uehara, Y.; Yamori, T. Anticancer Res. 2006, 26, 91‐97.

[11]. Lagoja, I. M. Chem. Biodiver. 2005, 2, 1‐50.
http://dx.doi.org/10.1002/cbdv.200490173

[12]. Dudhe, R.; Sharma, P. K.; Verma, P.; Chaudhary, A. J. Adv. Sci. Res. 2011, 2, 10‐17.

[13]. Yamazi, Y.; Takahashi, M.; Todome, Y. Proc. Soc. Exp. Biol. Med. 1970, 133, 674‐677.
http://dx.doi.org/10.3181/00379727-133-34542

[14]. Prichard, M. N.; Quenelle, D. C.; Hartline, C. B.; Harden, E. A.; Jefferson, G.; Frederick, S. L.; Daily, S. L.; Whitley, R. J.; Tiwari, K. N.; Maddry, J. A.; Secrist, J. A.; Kern, E. R. Antimicrob. Agents Chemother. 2009, 53, 5251‐5285.
http://dx.doi.org/10.1128/AAC.00417-09

[15]. Miyasaka, T.; Tanaka, H.; Baba, M.; Hayakawa, H.; Walker, R. T.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1989, 32, 2507‐2509.
http://dx.doi.org/10.1021/jm00132a002

[16]. Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Nitta, I.; Baba, M.; Shigeta, S.; Walker, R. T.; De Clercq, E.; Miyasaka, T. J. Med. Chem. 1992, 35, 337‐345.
http://dx.doi.org/10.1021/jm00080a020

[17]. Balzarini, J.; Baba, M.; De Clercq, E. Antimicrob. Agents Chemother. 1995, 39, 998‐1002.
http://dx.doi.org/10.1128/AAC.39.4.998

[18]. Fillios, L. C.; Naito, C.; Andrews, S.; Roach, A. M. Circ. Res. 1960, 8, 71‐77.
http://dx.doi.org/10.1161/01.RES.8.1.71

[19]. Kappe, C. O. Tetrahedron 1993, 49, 6937‐6963.
http://dx.doi.org/10.1016/S0040-4020(01)87971-0

[20]. Kreutzberger, A.; Burgwitz, K. Arch. Pharm. 1981, 314, 394‐398.
http://dx.doi.org/10.1002/ardp.19813140504

[21]. Monge, A.; Martinez‐Merino, V.; Sanmartin, C.; Fernandez, F. J.; Ochoa, M. C.; Bellver, C. Artigas, P. Arznei‐Forschung. 1990, 40, 1230‐1233.

[22]. Weitzel, K. W.; Wickman, J. M.; Augustin, S. G.; Strom, J. G. Clin. Ther. 2000, 22, 1254-1267.
http://dx.doi.org/10.1016/S0149-2918(00)83024-6

[23]. Yang, W.; Ruan, Z.; Wang, Y.; Van Kirk, K.; Ma, Z.; J. Arey, B.; Cooper, C. B.; Seethala, R.; Feyen, J. H. M.; Dickson, J. K. J. Med. Chem. 2009, 52, 1204-1208.
http://dx.doi.org/10.1021/jm801178c

[24]. Gillespie, R. J.; J. Bamford, S.; Botting, R.; Comer, M.; Denny, S.; Gaur, S.; Griffin, M.; Jordan, A. M.; Knight, A. R.; Lerpiniere, J.; Leonardi, S.; Lightowler, S.; McAteer, S. et al. V. J. Med. Chem. 2009, 52, 33-47.
http://dx.doi.org/10.1021/jm800961g

[25]. Tanaka, F.; Takeuchi, S.; Tanaka, N.; Yonehara, H.; Umezawa, H.; Sumiki, Y. J. Antibiot. 1961, 14, 161-162.

[26]. Reddick, J. J.; Saha, S.; Lee, J.; Melnick, J. S.; Perkins, J.; Begley, T. P. Bioorg. Med. Chem. Lett. 2001, 11, 2245-2248.
http://dx.doi.org/10.1016/S0960-894X(01)00373-0

[27]. Stenbuck, P.; Hood, H. M. 1962, US Patent 3, 049, 544.

[28]. Brogden, R. N.; Carmine, A. A.; Heel, R. C.; Speight, T. M.; Avery, G. S Drugs 1982, 23, 405-430.
http://dx.doi.org/10.2165/00003495-198223060-00001

[29]. Hughes, W. T.; Feldman, S.; Sanyal, S. K. T. Can. Med. Assoc J. 1975, 112, 47-50.

[30]. Hertel, L. W.; Border, G. B.; Kroin, J. S.; Rinzel, S. M.; Poore, G. A.; Todd, G. C.; Grindey, G. B. Cancer Res. 1990, 50, 4417-4422.

[31]. Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Science 1999, 286, 971‐974.
http://dx.doi.org/10.1126/science.286.5441.971

[32]. Sharp, D. J.; Rogers, G. C.; Scholey, J. M. Nature 2000, 407, 41‐47.
http://dx.doi.org/10.1038/35024000

[33]. Parikh, K. S.; Vyas, S. P. Asian J. Biochem. Res. 2012, 2, 1-7.

[34]. Gulcan, M.; Sonmez, M.; Berber, I. Turk. J. Chem. 2012, 36, 189-200.

[35]. Kalpesh, S. P.; Sandip, P. V. der Pharm. Lett. 2012, 4, 638-640.

[36]. Davis, A. L.; Keeler, J.; Laue, E. D.; Moskau, D. J. Magn. Reson. 1992, 98, 207‐216.

[37]. Abraham, E. P.; Chain, C. M.; Fletcher, A. D.; Gardner, N. G.; Heatly, M. A. Jennings, H. W. Lancet 1941, 238, 177-1989.
http://dx.doi.org/10.1016/S0140-6736(00)72122-2

[38]. Seeliger, S.; de Groot, B. L. J. Comput. Aid. Mol. Des. 2010, 24, 417‐422.
http://dx.doi.org/10.1007/s10822-010-9352-6

[39]. Onuffer, J. J.; Ton, B. T.; Kleent, I.; Kirsch, J. F. Protein Sci. 1995, 4, 1743-1749.
http://dx.doi.org/10.1002/pro.5560040909

[40]. Zhan, P.; Liu, X.; Li, Z.; Fang, Z.; Pannecouque, C.; De Clercq, E. Chem. Biodivers. 2010, 7, 1717‐1727.
http://dx.doi.org/10.1002/cbdv.200900197

Supporting Agencies

Most read articles by the same author(s)

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).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics