European Journal of Chemistry 2014, 5(2), 351-355 | doi: https://doi.org/10.5155/eurjchem.5.2.351-355.1010 | Get rights and content






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Computational study and antimicrobial activity of few Dapsone Schiff base derivatives


Wasfi Abood Al-Masoudi (1,*) , Tamadher Mohammad Al-Tememy (2) , Rafid Hmedan Al-Assadi (3)

(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 Chemistry College of Education, University of Basrah, Basrah, 61001, Iraq
(*) Corresponding Author

Received: 04 Jan 2014 | Accepted: 28 Feb 2014 | Published: 30 Jun 2014 | Issue Date: June 2014

Abstract


Condensation of 4,4-diaminodiphenyl sulfone (Dapsone) with aliphatic and aromatic aldehydes yielded a few Schiff base derivatives in good yields. The optimized structural parameters (bond lengths and bond angles) of three azomethine compounds have been obtained by using the GAUSSIAN 09 program package. Conformer of compound 1 has the highest energy, which has less stability than compounds 2 and 3 at the same model. The synthesized compounds were screened for antibacterial activity against Staphylococcus aureus, Escherichia coli, Bacillus subtilis and fungicidal activity against Aspergillus niger and Candida albicans. All compounds exhibited potent antibacterial and antifungal activity with the reference standard ciprofloxacin and Amphotericin B, respectively.


Keywords


DFT; Dapsone; Schiff base; Antimicrobial; NMR spectroscopy; Computational study

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DOI: 10.5155/eurjchem.5.2.351-355.1010

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Funding information


University of Basrah, Basrah, Iraq

References

[1]. Schiff, H. Ann. Chem. 1846, 131, 118-119.
http://dx.doi.org/10.1002/jlac.18641310113

[2]. Schiff, H. Ann. Chem. 1864, 3, 343-345.

[3]. Schiff, H. Ann. Chem. 1869, 150, 193-200.
http://dx.doi.org/10.1002/jlac.18691500206

[4]. Gemi, M. J.; Biles, C.; Keiser, B. J.; Poppe, S. M.; Swaney, S. M.; Tarapley, W. G.; Romeso, D. L.; Yage, Y. J. Med. Chem. 2000, 43(5), 1034-1040.
http://dx.doi.org/10.1021/jm990383f

[5]. Al-Masoudi, W. A.; Tooama, H.; J. Hammed, Basrah J. Vet. Res. 2014, 7, 33, inpress.

[6]. Lednicer, D. S. The Organic Chemistry of Drug Synthesis, Vol. 11, New York, 27, pp. 412, 1980.

[7]. Kumar, A; Singh, G.; Handa, R. N. Indian J. Chem. 1999, 38A, 613-617.

[8]. Foye, W. O. Principles of Medicinal Chemistry, 3rd edition, Varghese Publishing House, Bombay, 1989, 728.

[9]. Guo, Z. Y.; Xing, R.; Liu, S.; Zhong, Z.; Ji, X.; Wang, L.; Li, P. C. Carbohydrate Res. 2007, 342(10), 1329-1332.
http://dx.doi.org/10.1016/j.carres.2007.04.006

[10]. Wadher, S. J.; Puranik, M. P.; Karande, N. A.; Yeole, P. G. Int. J. Pharm. Tech. Res. 2009, 1(1), 22-33.

[11]. Spinu, C.; Pleniceanu, M.; Tigae, C. Turk. J. Chem. 2008, 32, 487-493.

[12]. Temel, H.; Hosgoren, H. Trans. Met. Chem. 2002, 27(6), 609-612.
http://dx.doi.org/10.1023/A:1019863131261

[13]. Frisch, M. J.; Trucks G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O; A. J. Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc., Gaussian 09, Revision A. 02, Wallingford CT, 2009.

[14]. Al-Rubaie, A. Z.; Al-Masoudi, W. A.; Al-Jadaan, S. A.; Jalbout, A. F; Hameed, A. J. Heteroatom Chem. 2008, 19(3), 307-315.
http://dx.doi.org/10.1002/hc.20437

[15]. Ovidiu, O.; Joseph, T. N.; Cristina, M.; Brindusa, T.; Smaranda, O.; Adrian, P.; Laurian, V.; Aurian, V.; Philippe, V. Farmacia 2012, 60(6), 785-797.

[16]. Wang, Y. H.; Zou, J. W.; Zhang, B.; Jin, Y. X. and Yu, Q, S. J. Mol. Struct. Theochem. 2005, 755, 31-37.
http://dx.doi.org/10.1016/j.theochem.2005.06.029

[17]. Zhang, Y; Monga, V.; Wang, Y. J. Phys. Chem. 2008, 112, 3231-3238.

[18]. Dhayakala, P. U.; Jayanthi, A.; Rajendiran, T. V.; Gunasekaran, S. Inter. J. Chem. Tech. Res. 2001, 3, 1851-1862.

[19]. Rajeev, S.; Kumar, D.; Bhoop, S.; Singh, V.; Ranjana, S. Res. J. Chem. Sci. 2013, 3, 79-84.

[20]. Alaghaz, A. M. A. and Ammar, R. A. Eur. J. Med. Chem. 2010, 45, 1314-1322.
http://dx.doi.org/10.1016/j.ejmech.2009.12.008

[21]. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
http://dx.doi.org/10.1063/1.448799

How to cite


Al-Masoudi, W.; Al-Tememy, T.; Al-Assadi, R. Eur. J. Chem. 2014, 5(2), 351-355. doi:10.5155/eurjchem.5.2.351-355.1010
Al-Masoudi, W.; Al-Tememy, T.; Al-Assadi, R. Computational study and antimicrobial activity of few Dapsone Schiff base derivatives. Eur. J. Chem. 2014, 5(2), 351-355. doi:10.5155/eurjchem.5.2.351-355.1010
Al-Masoudi, W., Al-Tememy, T., & Al-Assadi, R. (2014). Computational study and antimicrobial activity of few Dapsone Schiff base derivatives. European Journal of Chemistry, 5(2), 351-355. doi:10.5155/eurjchem.5.2.351-355.1010
Al-Masoudi, Wasfi, Tamadher Mohammad Al-Tememy, & Rafid Hmedan Al-Assadi. "Computational study and antimicrobial activity of few Dapsone Schiff base derivatives." European Journal of Chemistry [Online], 5.2 (2014): 351-355. Web. 22 Oct. 2020
Al-Masoudi, Wasfi, Al-Tememy, Tamadher, AND Al-Assadi, Rafid. "Computational study and antimicrobial activity of few Dapsone Schiff base derivatives" European Journal of Chemistry [Online], Volume 5 Number 2 (30 June 2014)

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DOI Link: https://doi.org/10.5155/eurjchem.5.2.351-355.1010

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