European Journal of Chemistry 2015, 6(2), 127-130 | doi: https://doi.org/10.5155/eurjchem.6.2.127-130.1175 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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


Wasfi Abood Al-Masoudi (1,*) , Abeer Laily Mohmmed (2) , Wamedh Hashim Abass (3) , Najim Aboud Al-Masoudi (4)

(1) Department of Physiology and Chemistry, College of Veterinary, University of Basrah, Basrah, 61001, Iraq
(2) Department of Microbiology, College of Veterinary, University of Basrah, Basrah, 61001, Iraq
(3) Department of Public Health, College of Veterinary, University of Basrah, Basrah, 61001, Iraq
(4) Department of Chemistry, College of Science, University of Basrah, Basrah, 61001, Iraq
(*) Corresponding Author

Received: 27 Oct 2014 | Accepted: 27 Nov 2014 | Published: 30 Jun 2015 | Issue Date: June 2015

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.


Keywords


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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.6.2.127-130.1175

Links for Article


| | | | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 719 times | PDF Article downloaded 300 times


Citations

/


[1]. Ganbing Yao, Zhanxiang Xia, Zhihui Li
Thermodynamic study of solubility for 2-amino-4-chloro-6-methoxypyrimidine in twelve organic solvents at temperatures from 273.15 K to 323.15 K
The Journal of Chemical Thermodynamics  105, 187, 2017
DOI: 10.1016/j.jct.2016.10.020
/


[2]. Antonio Guirado, Enrique Alarcón, Yesica Vicente, Raquel Andreu, Delia Bautista, Jesús Gálvez
A new convenient synthetic approach to diarylpyrimidines
Tetrahedron  72(27-28), 3922, 2016
DOI: 10.1016/j.tet.2016.05.018
/


[3]. Wasfi Aboud Al-Masoudi, Rana Adnan Faaz, Rafid Hmedan Al-Asadi, Hazim Saad Jabbar
Synthesis, antimicrobial activity and modelling studies of some new metal complexes of Schiff base derived from sulphonamide drug in vitro
European Journal of Chemistry  7(1), 102, 2016
DOI: 10.5155/eurjchem.7.1.102-106.1374
/


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

How to cite


Al-Masoudi, W.; Mohmmed, A.; Abass, W.; Al-Masoudi, N. Eur. J. Chem. 2015, 6(2), 127-130. doi:10.5155/eurjchem.6.2.127-130.1175
Al-Masoudi, W.; Mohmmed, A.; Abass, W.; Al-Masoudi, N. Synthesis, antimicrobial activity and molecular modeling study of some new pyrimidine derivatives. Eur. J. Chem. 2015, 6(2), 127-130. doi:10.5155/eurjchem.6.2.127-130.1175
Al-Masoudi, W., Mohmmed, A., Abass, W., & Al-Masoudi, N. (2015). Synthesis, antimicrobial activity and molecular modeling study of some new pyrimidine derivatives. European Journal of Chemistry, 6(2), 127-130. doi:10.5155/eurjchem.6.2.127-130.1175
Al-Masoudi, Wasfi, Abeer Laily Mohmmed, Wamedh Hashim Abass, & Najim Aboud Al-Masoudi. "Synthesis, antimicrobial activity and molecular modeling study of some new pyrimidine derivatives." European Journal of Chemistry [Online], 6.2 (2015): 127-130. Web. 27 May. 2020
Al-Masoudi, Wasfi, Mohmmed, Abeer, Abass, Wamedh, AND Al-Masoudi, Najim. "Synthesis, antimicrobial activity and molecular modeling study of some new pyrimidine derivatives" European Journal of Chemistry [Online], Volume 6 Number 2 (30 June 2015)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item


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

| | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2015, 6(2), 127-130 | doi: https://doi.org/10.5155/eurjchem.6.2.127-130.1175 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  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 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort