European Journal of Chemistry

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



Main Article Content

Shadia Ahmed Galal
Ahmed S. Abdelsamie
Mireya L. Rodriguez
Sean M. Kerwin
Hoda I. El Diwani

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 2898 times | icon graph Article PDF downloaded 1375 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
Crossref - Scopus - Google - European 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).