European Journal of Chemistry

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



Main Article Content

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.


icon graph This Abstract was viewed 1557 times | icon graph Article PDF downloaded 731 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
Crossref - Scopus - Google - European 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

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 © 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).