European Journal of Chemistry

Synthesis, antimicrobial activity, computational and modeling studies of some new organotellurium compounds containing azo moities



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Wasfi Aboud Al-Masoudi
Rafid Hmedan Al-Asadi
Rasha Munther Othman
Najim Aboud Al‐Masoudi

Abstract

A new series of organonotellurium compounds containing azo groups were prepared by new and convenient methods. Reaction of 1-(4-mercuric chloride-2,3-dichlorophenyl)-2-chloro diazine (4) with 8-hydroxyquinoline (5) gave the new organomercury compound 6 in good yield. Telluratio of compound 6 with tellurium tetrabromide in 1:1 and 1:2 mole ratio gave the o-tellurated azo compounds ArTeBr3 (7) and Ar2TeBr2 (9), respectively. Reduction of both ArTeBr3 and Ar2TeBr2 by hydrazine hydrate gave the ditelluride 8, and telluride 10, respectively. The synthesized compounds were screened for their antibacterial activity against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Klebsiella pneumonia, Salmonella spp., Streptococcus spp. and Bacillus cereus. Additionally, the prepared compounds were tested for antifungal activity against Candida sp., Aspergillus multi and Aspergillus niger. All compounds exhibited good antibacterial and antifungal activity. Computational study of the new compounds was calculated using Gaussian 09 program package. Molecular modeling studies were performed and showed hydrogen binding and hydrophobic interactions.


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Al-Masoudi, W. A.; Al-Asadi, R. H.; Othman, R. M.; Al‐Masoudi, N. A. Synthesis, Antimicrobial Activity, Computational and Modeling Studies of Some New Organotellurium Compounds Containing Azo Moities. Eur. J. Chem. 2015, 6, 374-380.

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References

[1]. Engman, L.; Stern, D.; Cotgreave, I. A.; Anderson, C. M. J. Am. Chem. Soc. 1992, 114, 9737-9343.
http://dx.doi.org/10.1021/ja00051a002

[2]. Nogueira, C. W.; Zeni, G.; Rocha, B. T. Chem. Rev. 2004, 104, 6255-6285.
http://dx.doi.org/10.1021/cr0406559

[3]. Chasteen, T. G.; Bentley, R. Chem. Rev. 2003, 103, 1-25.
http://dx.doi.org/10.1021/cr010210+

[4]. Cunha, R. L.; Urano, M. E.; Chagas, J. R.; Almeida, P. C.; Bincoletto, C.; Tersario, I. L.; Comasseto, J. V. Bioorg. Med. Chem. Lett. 2005, 15, 755-760.
http://dx.doi.org/10.1016/j.bmcl.2004.11.012

[5]. Abondanza, T. S.; Oliveira, C. R.; Barbosa, C. M.; Pereira, F. E.; Cunha, R. L.; Caires, A. C.; Comasseto, J. V.; Queiroz, M. L.; Valadares, M. C. Bincoletto, C. Food Chem. Toxicol. 2008, 46, 2550-2545.

[6]. Wieslander, E.; Engman, L.; Svensjoe, E.; Erlansson, M.; Johansson, U.; Linden, M.; Andersson, C. M.; Brattsand, R. Biochem. Pharmacol. 1998, 55, 573-584.
http://dx.doi.org/10.1016/S0006-2952(97)00517-0

[7]. Garberg, P.; Engman, L.; Tolmachev, V.; Lundqvist, H.; Gerdes, R. G.; Cotgreave, I. A. Int. J. Biochem. Cell Biol. 1999, 31, 291-301.
http://dx.doi.org/10.1016/S1357-2725(98)00113-7

[8]. Sailer, B. L.; Liles, N.; Dickerson, S.; Chasteen, T. G. Arch. Toxicol. 2003, 77, 30-36.
http://dx.doi.org/10.1007/s00204-002-0407-x

[9]. Serdni, B.; Xu, R. H.; Albeck, M.; Gafter, U.; Gal, Shani, A.; Tichler, T.; Shapira, J.; Bruderman, I.; Catane, R.; Kaufman, B.; Whisnant, J. K.; Metinger, K. L.; Kalechman, Y. Int. J. Cancer 1996, 65, 97-103.

[10]. Brodsky, M.; Halpert, G.; Sredni, B. J. Inflamm. 2010, 7, 3-7.
http://dx.doi.org/10.1186/1476-9255-7-3

[11]. Serdni, B.; Weil, M.; I. Khomenok, G.; Lebenthal, I.; Teitz, S.; Mardor, Y.; Ram, Z.; Orenstein, A.; Kershenovich, S.; Michowiz, S. Cancer Res. 2004, 64, 1853-1852.

[12]. Sredni, B.; Caspi, R. R.; Klein, A.; Kalechman, Y.; Danziger, Y. Nature 1987, 330, 173-176.
http://dx.doi.org/10.1038/330173a0

[13]. Sredni, B.; Gal, R.; Cohen, I. J.; Dazard, J. E.; Givol, D.; Gafter, U. FASEB J. 2004, 18, 400-402.

[14]. Barbara, C.; Lima, C.; Arrais-Silva, W. W.; Oliveira, R. L.; Cunha, R.; Giogio, S. Korean J. Parasaitol. 2009, 47, 213-218.
http://dx.doi.org/10.3347/kjp.2009.47.3.213

[15]. Cobbledick, R. E.; Einstein, F. W. B.; McWhinnie, W. R.; Musa, F. H. J. Chem. Soc. (S) 1979, 145, 1901.

[16]. Al-Rubaie, A. Z.; Al-Salim, N. I.; Al-Jaddan, S. A. N. J. Organomet. Chem. 1993, 443, 67-70.
http://dx.doi.org/10.1016/0022-328X(93)80010-9

[17]. Al-Rubaie, A. Z.; Fingan, A. M.; Al-Salim, N. I.; Al-Jadaan, S. A. N. Polyhydron 1994, 14, 2575-2579.
http://dx.doi.org/10.1016/0277-5387(95)00001-9

[18]. Singh, H. B.; McWhinnie, W. R. J. Chem. Soc. Dalton Trans 1985, 821-825.
http://dx.doi.org/10.1039/dt9850000821

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

[20]. Singh, H. B.; Sudha, N.; West, A. A.; Hamor, T. A. J. Chem. Soc. Dalton Trans 1990, 907-913
http://dx.doi.org/10.1039/dt9900000907

[21]. Al-Rubaie, A. Z.; Al-Salim, N. I.;Al-Jadaan, S. A. N. J. Organomet. Chem. 1993, 443, 67-70.
http://dx.doi.org/10.1016/0022-328X(93)80010-9

[22]. Saadon, H. L.; Al-Fregi, A. A. Optics Laser Techn. 2014, 58, 33-38.
http://dx.doi.org/10.1016/j.optlastec.2013.10.032

[23]. Inui, T.; Yamanishi, K.; Sato, E.; Matsumoto, A. Macromolecules 2013, 46, 8111-8120.
http://dx.doi.org/10.1021/ma401595w

[24]. Nakamura, Y.; Yamago, S. S. Beilstein J. Org. Chem. 2013, 9, 1607-1612.
http://dx.doi.org/10.3762/bjoc.9.183

[25]. Al-Asadi, R. H.; Fahad, T. A.; Saeed, B. A. J. Adv. Chem. 2014, 9, 2078-2082.

[26]. Al-Masoudi, W. A. J. Univ. Zakho 2013, 1, 387-393.

[27]. 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. Gaussian, Inc., Gaussian 09, Revision A. 02, Wallingford CT, 2009.

[28]. Becke, A. D. J. Chem. Phys. 1997, 107, 8554-8560.
http://dx.doi.org/10.1063/1.475007

[29]. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-299.
http://dx.doi.org/10.1063/1.448799

[30]. Mohammed, I. M.; Mustapha, A. Molecules 2010, 15, 7498-7508.
http://dx.doi.org/10.3390/molecules15107498

[31]. Shah, S. N. N; Basser M. A. Asian J. Pharm. Clin. Res. 2012, 5, 146-149.

[32]. Davis, W. M.; Goddard, J. D. Can. J. Chem. 1996, 74, 810-818.
http://dx.doi.org/10.1139/v96-089

[33]. Minkin, V. I.; Minyaev, R. M. Mendelleev Commun. 2000, 10, 171-173.
http://dx.doi.org/10.1070/MC2000v010n05ABEH001349

[34]. Chandrasekhar, V.; Kumur, A.; Pandy, D. J. Organomet. Chem. 2010, 695, 74-81.
http://dx.doi.org/10.1016/j.jorganchem.2009.09.030

[35]. Chauhan, A. K.; Bharti, S. N.; Srivastava, R. C.; Butcher, R. J.; Duthi, A. J. Organomet. Chem. 2013, 728, 38-43.
http://dx.doi.org/10.1016/j.jorganchem.2013.01.010

[36]. Casagrande, G. A.; Raminelli, C.; Lang, E. S.; Lemos, S. S. Inorg. Chim. Acta 2011, 365, 492-495.
http://dx.doi.org/10.1016/j.ica.2010.09.053

[37]. Ledesma, G. N.; Lang, E.; Vazquez-Lopez, E. M.; Abram, V. Inorg. Chem. Commun. 2004, 7, 478-480.
http://dx.doi.org/10.1016/j.inoche.2004.01.007

[38]. Detly, M. R. The Chemistry of HetrocyclicCompounbs, John Wiley & Sons, Inc. 1994.

[39]. Panda, A.; Panda, S.; Srivastava, K.; Singh, H. B. Inorg. Chimica Acta 2011, 372, 17-31.
http://dx.doi.org/10.1016/j.ica.2011.02.031

[40]. Chauhan, A. K.; Singh, P.; Srivastava, R. C.; Butcher, R.; Duthie, A. Inorg. Chim. Acta 2011, 376, 80-86.
http://dx.doi.org/10.1016/j.ica.2011.05.039

[41]. Lewis, D. F.; Loannides, C.; Parke, D. V. Xenobiotica 1994, 24, 401-408.
http://dx.doi.org/10.3109/00498259409043243

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

[43]. 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

[44]. Seeliger, S.; DeGroot, B. L. J. Comp.-Aided Mol. Design 2010, 24, 417-422.
http://dx.doi.org/10.1007/s10822-010-9352-6

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Departments of Physiology and Microbiology, College of Veterinary Medicine, Basrah University, Iraq
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