European Journal of Chemistry

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

Article Sidebar

PDF
Published: Dec 31, 2015
DOI: https://doi.org/10.5155/eurjchem.6.4.374-380.1254
Keywords:
LANL2DZ, Telluration, Azo compounds, 8-Hydroxyquinoline, Antimicrobial activity, Computational and modeling studies
Section
Research Article
Issue
Vol. 6 No. 4 (2015): December 2015
Dates
Received 2015-02-07
Accepted 2015-03-28
Published 2015-12-31


Main Article Content

Wasfi Aboud Al-Masoudi
Department of Physiology and Chemistry, College of Veterinary, University of Basrah, Basrah, 61001, Iraq
Rafid Hmedan Al-Asadi
Department of Chemistry, College of Education for Pure Sciences, University of Basrah, 61001, Basrah, Iraq
Rasha Munther Othman
Department of Microbiology, 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

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.


icon graph This Abstract was viewed 1906 times | icon graph Article PDF downloaded 938 times

How to Cite
(1)
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.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
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

Supporting Agencies

Departments of Physiology and Microbiology, College of Veterinary Medicine, Basrah University, Iraq
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2025 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).