European Journal of Chemistry 2010, 1(2), 67-72 | doi: https://doi.org/10.5155/eurjchem.1.2.67-72.1 | Get rights and content

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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


Shadia Ahmed Galal (1,*) , Ahmed S. Abdelsamie (2) , Mireya L. Rodriguez (3) , Sean M. Kerwin (4) , Hoda I. El Diwani (5)

(1) Department of Chemistry of Natural and Microbial Products, Division of Pharmaceutical and Drug Industries Research, National Research Centre, Dokki, 12622, Cairo, Egypt
(2) Department of Chemistry of Natural and Microbial Products, Division of Pharmaceutical and Drug Industries Research, National Research Centre, Dokki, 12622, Cairo, Egypt
(3) Department of Chemistry and Biochemistry, Division of Medicinal Chemistry and Institute for Cellular and Molecular Biology, The University of Texas, Austin, TX 78712 USA
(4) Department of Chemistry and Biochemistry, Division of Medicinal Chemistry and Institute for Cellular and Molecular Biology, The University of Texas, Austin, TX 78712 USA
(5) Department of Chemistry of Natural and Microbial Products, Division of Pharmaceutical and Drug Industries Research, National Research Centre, Dokki, 12622, Cairo, Egypt
(*) Corresponding Author

Received: 23 Mar 2010 | Revised: 29 Apr 2010 | Accepted: 30 Apr 2010 | Published: 15 Jun 2010 | Issue Date: June 2010

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


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).

2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).

3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


Salicylate; Hydrogen bonding; DFT-Molecular dynamics; Vibrational spectroscopy; Relaxation spectroscopy

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.1.2.67-72.1

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 2436 times | icon graph PDF Article downloaded 1133 times

Funding information


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

Citations

/


[1]. Deepak Sharma, Hari Om, Ashok Kumar Sharma
Potential Synthetic Routes and Metal-Ion Sensing Applications of 1,3,4-Oxadiazoles: An Integrative Review
Critical Reviews in Analytical Chemistry  , 1, 2022
DOI: 10.1080/10408347.2022.2080494
/

[2]. Leyla Yurttaş, Gülşen Akalin Çiftçi, Mehmet Onur Aksoy, Şeref Demirayak
Novel Benzimidazole Derivatives: Cytotoxic and Apoptotic Properties on Lung Cancer Cell Line
Letters in Drug Design & Discovery  17(10), 1227, 2020
DOI: 10.2174/1570180817999200513091613
/

[3]. Aboli Sapkal, Santosh Kamble
Greener and Environmentally Benign Methodology for the Synthesis of Pyrazole Derivatives
ChemistrySelect  5(42), 12971, 2020
DOI: 10.1002/slct.202003008
/

[4]. Lobna Abdel-Mohsen Ebaid Nassr, Ali Momamad Shaker
Kinetic and Mechanistic Aspects of Reactivity of the Oxidation of Some Fe(II)-Tris Schiff Base Complexes by Peroxydisulfate: Spectrophotometric Tracer and Solvent Effect on the Reactivity
International Journal of Chemical Kinetics  46(11), 701, 2014
DOI: 10.1002/kin.20880
/

[5]. Keisham S. Singh, Francis Joy, Prabha Devi
Ruthenium(II)-catalyzed synthesis of 2-arylbenzimidazole and 2-arylbenzothiazole in water
Transition Metal Chemistry  46(3), 181, 2021
DOI: 10.1007/s11243-020-00435-3
/

[6]. Marwa F. Ahmed, Amany Belal, Mahmoud Youns
Design, synthesis, molecular modeling and anti-breast cancer activity of novel quinazolin-4-one derivatives linked to thiazolidinone, oxadiazole or pyrazole moieties
Medicinal Chemistry Research  24(7), 2993, 2015
DOI: 10.1007/s00044-015-1357-1
/

[7]. Suresh Seeka, Sirassu Narsimha, Kumaraswamy Battula, Althaf Hussain Shaikh, Savitha Jyostna Tangeda, Vasudeva Reddy Nagavelli
One pot synthesis of 1-((1-aryl-1H-1,2,3-triazol-4-yl)methyl)-1H-benzo[d] imidazoles in ionic liquids: Evaluation of antioxidant and antimicrobial activities
European Journal of Chemistry  6(4), 482, 2015
DOI: 10.5155/eurjchem.6.4.482-487.1325
/

[8]. Kumaraswamy Gullapelli, G. Brahmeshwari, M. Ravichander, Uma Kusuma
Synthesis, antibacterial and molecular docking studies of new benzimidazole derivatives
Egyptian Journal of Basic and Applied Sciences  4(4), 303, 2017
DOI: 10.1016/j.ejbas.2017.09.002
/

[9]. V. Anil, B. Shankar, G. Bharath, P. Jalapathi
Synthesis and Antimicrobial Activity of Novel Substituted 4-[3-(1H-Benzimidazol-2-yl)-4-hydroxybenzyl]-2-(1H-benzimidazol-2-yl)phenol Derivatives
Russian Journal of General Chemistry  87(12), 3017, 2017
DOI: 10.1134/S1070363217120477
/

[10]. Leyla Yurttaş, Şeref Demirayak, Gülşen A. Çiftçi, Şafak Ulusoylar Yıldırım, Zafer A. Kaplancıklı
Synthesis and Biological Evaluation of Some 1,2-Disubstituted Benzimidazole Derivatives as New Potential Anticancer Agents
Archiv der Pharmazie  346(5), 403, 2013
DOI: 10.1002/ardp.201200452
/

[11]. Manmohan Reddy Depa, Suneetha Potla, Umesh C. Narkhede, Vinod D. Jadhav, Siddaiah Vidavalur
Cu(I)-Promoted Regioselective Synthesis of Some New Benzimidazole-1,2,3-Triazole Frameworks as In Vitro Anticancer Agents
Russian Journal of Bioorganic Chemistry  47(5), 1028, 2021
DOI: 10.1134/S1068162021050228
/

[12]. V. Anil, B. Shankar, G. Bharath, P. Jalapathi
Synthesis and antimicrobial activity of novel substituted 4-[3-(1H-benzimidazol-2-yl)-4-hydroxybenzyl]-2-(1H-benzimidazol-2-yl)phenol derivatives
Russian Journal of General Chemistry  87(11), 2648, 2017
DOI: 10.1134/S1070363217110202
/

[13]. K J Al-adilee, B A Hatem, O A Hatem
Synthesis and spectral characterization of new azo dye derived from benzimidazole and its complexation with selected transition metal ions
Journal of Physics: Conference Series  1999(1), 012123, 2021
DOI: 10.1088/1742-6596/1999/1/012123
/

[14]. Shadia A. Galal, Muhammad Khattab, Fotini Andreadaki, Evangelia D. Chrysina, Jean-Pierre Praly, Fatma A.F. Ragab, Hoda I. El Diwani
Synthesis of (benzimidazol-2-yl)aniline derivatives as glycogen phosphorylase inhibitors
Bioorganic & Medicinal Chemistry  24(21), 5423, 2016
DOI: 10.1016/j.bmc.2016.08.069
/

[15]. A. Ashma, A. Sudha, S.L. Ashok Kumar, G. Sasikumar, S.J. Askar Ali
One Pot Synthesis of Schiff Base Complexes of Cu(II), Zn(II), Ni(II), Co(II) and their Cytotoxicity, Molecular Docking and Antibacterial Activity
Asian Journal of Chemistry  32(10), 2507, 2020
DOI: 10.14233/ajchem.2020.
/

[16]. Hala Bakr El-Nassan
Synthesis, antitumor activity and SAR study of novel [1,2,4]triazino[4,5-a]benzimidazole derivatives
European Journal of Medicinal Chemistry  53, 22, 2012
DOI: 10.1016/j.ejmech.2012.03.028
/

[17]. Bhookya Shankar, Pochampally Jalapathi, Balabadra Saikrishna, Shaym Perugu, Vijjulatha Manga
Synthesis, anti-microbial activity, cytotoxicity of some novel substituted (5-(3-(1H-benzo[d]imidazol-2-yl)-4-hydroxybenzyl)benzofuran-2-yl)(phenyl)methanone analogs
Chemistry Central Journal  12(1), , 2018
DOI: 10.1186/s13065-017-0364-3
/

[18]. Kumaraswamy Gullapelli, Ravichandar Maroju, Ramchander Merugu
Synthesis, In-vitro and In-silico Anti-inflammatory activity of new Thiazole derivatives
Research Journal of Pharmacy and Technology  , 4253, 2021
DOI: 10.52711/0974-360X.2021.00738
/

[19]. O A Hatem, K J Al-Adilee, B A Hatem
Theoretical Study of the Azo Dye Derived From 2-[6-(benzimidazolyl)azo]-2,4-di chloro phenol and Its Metal Complexes
Journal of Physics: Conference Series  1664(1), 012054, 2020
DOI: 10.1088/1742-6596/1664/1/012054
/

[20]. Magdy Ahmed Ibrahim
Synthetic Utilities of o-Phenylenediamines: Synthetic Approaches for Benzimidazoles, Quinoxalines and Benzo[1,5]diazepines
HETEROCYCLES  83(12), 2689, 2011
DOI: 10.3987/REV-11-713
/

[21]. Mohamed A. Omar, Yasser M. Shaker, Shadia A. Galal, Mamdouh M. Ali, Sean M. Kerwin, Jing Li, Harukuni Tokuda, Raghda A. Ramadan, Hoda I. El Diwani
Synthesis and docking studies of novel antitumor benzimidazoles
Bioorganic & Medicinal Chemistry  20(24), 6989, 2012
DOI: 10.1016/j.bmc.2012.10.010
/

[22]. Kumar Vasantha, Guru Basavarajaswamy, M. Vaishali Rai, Poojary Boja, Vinitha R. Pai, N. Shruthi, Mahima Bhat
Rapid ‘one-pot’ synthesis of a novel benzimidazole-5-carboxylate and its hydrazone derivatives as potential anti-inflammatory and antimicrobial agents
Bioorganic & Medicinal Chemistry Letters  25(7), 1420, 2015
DOI: 10.1016/j.bmcl.2015.02.043
/

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


How to cite


Galal, S.; Abdelsamie, A.; Rodriguez, M.; Kerwin, S.; El Diwani, H. Eur. J. Chem. 2010, 1(2), 67-72. doi:10.5155/eurjchem.1.2.67-72.1
Galal, S.; Abdelsamie, A.; Rodriguez, M.; Kerwin, S.; El Diwani, H. 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(2), 67-72. doi:10.5155/eurjchem.1.2.67-72.1
Galal, S., Abdelsamie, A., Rodriguez, M., Kerwin, S., & El Diwani, H. (2010). Synthesis and studying the antitumor activity of novel 5-(2-methylbenzimidazol-5-yl)-1,3,4-oxadiazole-2(3H)-thiones. European Journal of Chemistry, 1(2), 67-72. doi:10.5155/eurjchem.1.2.67-72.1
Galal, Shadia, Ahmed S. Abdelsamie, Mireya L. Rodriguez, Sean M. Kerwin, & Hoda I. El Diwani. "Synthesis and studying the antitumor activity of novel 5-(2-methylbenzimidazol-5-yl)-1,3,4-oxadiazole-2(3H)-thiones." European Journal of Chemistry [Online], 1.2 (2010): 67-72. Web. 4 Oct. 2023
Galal, Shadia, Abdelsamie, Ahmed, Rodriguez, Mireya, Kerwin, Sean, AND El Diwani, Hoda. "Synthesis and studying the antitumor activity of novel 5-(2-methylbenzimidazol-5-yl)-1,3,4-oxadiazole-2(3H)-thiones" European Journal of Chemistry [Online], Volume 1 Number 2 (15 June 2010)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.1.2.67-72.1


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2010, 1(2), 67-72 | doi: https://doi.org/10.5155/eurjchem.1.2.67-72.1 | Get rights and content

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c)




© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.