European Journal of Chemistry

Synthesis and studying the antitumor activity of novel 5-(2-methylbenzimidazol-5-yl)-1,3,4-oxadiazole-2(3H)-thiones

Article Sidebar

PDF
Published: Jun 15, 2010
DOI: https://doi.org/10.5155/eurjchem.1.2.67-72.1
Keywords:
Salicylate, Hydrogen bonding, DFT-Molecular dynamics, Vibrational spectroscopy, Relaxation spectroscopy
Section
Research Article
Issue
Vol. 1 No. 2 (2010): June 2010
Dates
Received 2010-03-23
Accepted 2010-04-30
Published 2010-06-15


Main Article Content

Shadia Ahmed Galal
Department of Chemistry of Natural and Microbial Products, Division of Pharmaceutical and Drug Industries Research, National Research Centre, Dokki, 12622, Cairo, Egypt
Ahmed S. Abdelsamie
Department of Chemistry of Natural and Microbial Products, Division of Pharmaceutical and Drug Industries Research, National Research Centre, Dokki, 12622, Cairo, Egypt
Mireya L. Rodriguez
Department of Chemistry and Biochemistry, Division of Medicinal Chemistry and Institute for Cellular and Molecular Biology, The University of Texas, Austin, TX 78712 USA
Sean M. Kerwin
Department of Chemistry and Biochemistry, Division of Medicinal Chemistry and Institute for Cellular and Molecular Biology, The University of Texas, Austin, TX 78712 USA
Hoda I. El Diwani
Department of Chemistry of Natural and Microbial Products, Division of Pharmaceutical and Drug Industries Research, National Research Centre, Dokki, 12622, Cairo, Egypt

Abstract

The influence of the incorporation of 1,3,4-oxadiazole ring into 2-methyl-1H-benzimidazole derivatives producing a series of substituted 5(6)-(2-methylbenzimidazol-5-yl)-1,3,4-oxadiazoles on the antitumor activity was studied in this study. The antitumor activity of the new compounds was tested against breast cancer cell line MCF-7 and lung cancer cell line A549. S-5-(2-methyl-1H-benzo[d]imidazol-5-yl)-1,3,4-oxadiazol-2-yl 2-nitrobenzenesulfonothioate (9) showed potent activity against both MCF-7 and A549 cell lines. Whereas, compounds 7, 11-13 and 15-17 have moderate growth inhibitory activity on the two cell lines.

1_2_67_72_800


icon graph This Abstract was viewed 2907 times | icon graph Article PDF downloaded 1394 times

How to Cite
(1)
Galal, S. A.; Abdelsamie, A. S.; Rodriguez, M. L.; Kerwin, S. M.; El Diwani, H. I. Synthesis and Studying the Antitumor Activity of Novel 5-(2-Methylbenzimidazol-5-Yl)-1,3,4-Oxadiazole-2(3H)-Thiones. Eur. J. Chem. 2010, 1, 67-72.

Article Details

Share
Links for Article


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

[1]. Aparicio, S.; Alcalde, R.; Dávila, M. J.; García, B.; Leal, J. M. J. Phys. Chem. B 2007, 111, 4417-4431.
doi:10.1021/jp068560t
PMid:17411084

[2]. Aparicio, S.; Alcalde, R. Green Chem. 2009, 11, 65-78.
doi:10.1039/b811909k

[3]. Yamada, H. Bull. Chem. Soc. Jpn. 1959, 32, 1051-1056.
doi:10.1246/bcsj.32.1051

[4]. Wojcik, M.J.; Paluszkiewicz, C. Can. J. Chem. 1983, 61, 1449-1452.
doi:10.1139/v83-253

[5]. Berthelot, M.; Laurence, C.; Lucon, M.; Rossignol, C. J. Phys. Org. Chem. 1996, 9, 626-630.
doi:10.1002/(SICI)1099-1395(199609)9:9<626::AID-POC828>3.0.CO;2-M

[6]. Mitsuzuka, A.; Fujii, A.; Ebata, T.; Mikami, N. J. Phys. Chem. A 1998, 102, 9779-9784.
doi:10.1021/jp9830934

[7]. Palomar, J.; De Paz, J. L. G.; Catalám, J. Chem. Phys. 1999, 246, 167-208.
doi:10.1016/S0301-0104(99)00159-7

[8]. Melandri, S.; Giuliano, B. M.; Maris, A.; Favero, L. B.; Ottaviani, P.; Velino, B.; Caminati, W. J. Phys. Chem. A. 2007, 111, 9076-9079.
doi:10.1021/jp0723970
PMid:17722889

[9]. Massaro, R. D.; Dai, Y.; Blaistein-Barojas, E. J. Phys. Chem. A 2009, 113, 10385-10390.
doi:10.1021/jp905887m
PMid:19708681

[10]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K.N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J.E.; Hratchian, H. P.; Cross, J.B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.;Rabuck,A.D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03 (Revision C.02), Gaussian, Inc., Wallingford CT, 2004.

[11]. Becke, A.D. Phys. Rev. A 1988, 38, 3098-3100.
doi:10.1103/PhysRevA.38.3098
PMid:9900728

[12]. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
doi:10.1103/PhysRevB.37.785

[13]. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.

[14]. Bader, R.F.W. Atoms in Molecules: a Quantum Theory, Oxford University Press, Oxford, 1990.

[15]. Biegler-König, F.; Schönbohm, J.; Bayles, D. J. Comput. Chem. 2001, 22, 545-559.
doi:10.1002/1096-987X(20010415)22:5<545::AID-JCC1027>3.0.CO;2-Y

[16]. Ponder, J. W. Tinker: Software tool for molecular design. 4.2 ed, Washington University School of Medicine, 2004.

[17]. Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. J. Am. Chem. Soc. 1996, 118, 11225-11236.
doi:10.1021/ja9621760

[18]. Aparicio, S.; Alcalde, R.; García, B.; Leal, J. M. Chem. Phys. Lett. 2007, 444, 252-257.
doi:10.1016/j.cplett.2007.07.033

[19]. Koch, U.; Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747-9754.
doi:10.1021/j100024a016

[20]. Popelier, P. L. A. J. Phys. Chem. A 1998, 102, 1873-1878.
doi:10.1021/jp9805048

[21]. Hibbs, D.E.; Overgaard, J.; Piltz, R.O. Org. Biomol. Chem. 2003, 1, 1191-1198.
doi:10.1039/b211683a

[22]. Espinosa, E.; Lecomte, C.; Molins, E. Chem. Phys. Lett. 1999, 300, 745-748.
doi:10.1016/S0009-2614(98)01399-2

[23]. Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170-173.
doi:10.1016/S0009-2614(98)00036-0

[24]. Varghese, H. T.; Panicker, C. Y.; Mannekutla, J. R.; Inamdar, S. R. Spectrochim. Acta A 2007, 66, 959–963.
doi:10.1016/j.saa.2006.04.034
PMid:16872885

Supporting Agencies

US-Egypt Joint Science and Technology Board Fund, Administered through the USDA (BIO9-002-015)
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 © 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).