2-Mercaptobenzimidazole Schiff Bases: Design, Synthesis, Antimicrobial Studies and Anticancer Activity on HCT-116 Cell Line

Author(s): Sumit Tahlan, Balasubramanian Narasimhan*, Siong Meng Lim, Kalavathy Ramasamy, Vasudevan Mani, Syed A.A. Shah

Journal Name: Mini-Reviews in Medicinal Chemistry

Volume 19 , Issue 13 , 2019


Become EABM
Become Reviewer
Call for Editor

Graphical Abstract:


Abstract:

Background: Increased rate of mortality due to the development of resistance to currently available antimicrobial and anticancer agents initiated the need to develop new chemical entities for the treatment of microbial infections and cancer.

Objective: The present study was aimed to synthesize and evaluate antimicrobial and anticancer activities of Schiff bases of 2-mercaptobenzimidazole.

Methods: The Schiff bases of 2-mercaptobenzimidazole were synthesized from 4-(2-(1H-benzo[d]- imidazol-2-ylthio)acetamido)benzohydrazide. The synthesized compounds were evaluated for antimicrobial and anticancer activities by tube dilution method and Sulforhodamine-B (SRB) assay, respectively.

Results: Compounds 8 (MICpa, an = 2.41, 1.20 µM/ml), 10 (MICse, sa = 2.50 µM/ml), 20 (MICec = 2.34 µM/ml) and 25 (MICca = 1.46 µM/ml) showed significant antimicrobial activity against tested bacterial and fungal strains and compounds 20 (IC50 = 8 µg/ml) and 23 (IC50 = 7 µg/ml) exhibited significant anticancer activity.

Conclusion: In general, the synthesized derivatives exhibited moderate antimicrobial and anticancer activities. Compounds 8 and 25 having high antifungal potential among the synthesized compounds may be taken as lead molecules for the development of novel antifungal agents.

Keywords: Antibacterial, anticancer, antifungal, 2-Mercaptobenzimidazole derivatives, SAR, mutagenicity.

[1]
Bandyopadhyay, P.; Sathe, M.; Ponmariappan, S.; Sharma, A.; Sharma, P.; Srivastava, A.K.; Kaushik, M.P. Exploration of in vitro time point quantitative evaluation of newly synthesized benzimidazole and benzothiazole derivatives as potential antibacterial agents. Bioorg. Med. Chem. Lett., 2011, 21, 7306-7309.
[2]
Desai, N.C.; Shihory, N.R.; Kotadiya, G.M. Facile synthesis of benzimidazole bearing 2-pyridone derivatives as potential antimicrobial agents. Chin. Chem. Lett., 2014, 25, 305-307.
[3]
Husain, A.; Rashid, M.; Shaharyar, M.; Siddiqui, A.A.; Mishra, R. Benzimidazole clubbed with triazolo-thiadiazoles and triazolo-thiadiazines: New anticancer agents. Eur. J. Med. Chem., 2013, 62, 785-798.
[4]
Garudachari, B.; Satyanarayana, M.N.; Thippeswamy, B.; Shivakumar, C.K.; Shivananda, K.N.; Hegde, G.; Isloor, A.M. Synthesis, characterization and antimicrobial studies of some new quinoline incorporated benzimidazole derivatives. Eur. J. Med. Chem., 2012, 54, 900-906.
[5]
Desai, K.G.; Desai, K.R. Green route for the heterocyclization of 2-mercaptobenzimidazole into β-lactum segment derivatives containing -CONH-bridge with benzimidazole: screening in vitro antimicrobial activity with various microorganisms. Bioorg. Med. Chem., 2006, 14(24), 8271-8279.
[6]
Gurrala, S.; Babu, Y.R.; Rao, G.V. latha, B.M. Symmetrical coupling of 2-mercapto benzimidazole derivatives and their antimicrobial activity. Int. J. Pharm. Pharm. Sci., 2011, 3, 217-220.
[7]
Anandarajagopal, K.; Tiwari, R.N.; Venkateshan, N.; Promwichit, P. Synthesis and charactrization of 2-mercapto benzimidazole derivatives as potential analgesic agents. Int. J. Chem. Pharm. Res., 2010, 2(3), 230-236.
[8]
Ozkay, U.D.; Ozkay, Y.; Can, O.D. Synthesis and analgesic effects of 2-(2-carboxyphenylsulfanyl)-N-(4-substitutedphenyl) acetamide derivatives. Med. Chem. Res., 2011, 20, 152-157.
[9]
Maske, P.P.; Lokapure, S.G.; Nimbalkar, D.; Disouza, J.I. Synthesis and antiprotozoal activity of nitro and halogeno substituted some novel mercaptobenzimidazole derivatives. Der. Pharma. Chemica, 2012, 4(3), 1283-1287.
[10]
Arora, R.; Gill, N.S.; Singh, N.; Rana, A.C. Microwave irradiation versus conventional method: Synthesis of some novel 2-substituted benzimidazole derivatives using Mannich Bases. Int. J. Chemtech Res., 2014, 6(2), 1110-1114.
[11]
Szanyi, I. lujber, L.; Gerlinger, I.; Pytel, J.; Bauer, M.; Csejtey, A.; Szele, E.; Gombos, K.; Kiss, I.; Seredenin, S.; Yarkova, M.; Ember, L. In vivo effects of afobazole (2-mercaptobenzimidazole derivative) on the 7,12-dimethylbenz [d]anthracene-induced oncogene and suppressor gene expression. In Vivo, 2007, 21, 1059-1064.
[12]
Gupta, S.K.; Pancholi, S.S. Synthesis and evaluation of antitubercular activity of some thiobenzimidazolyl derivatives. Der. Pharma. Chemica, 2011, 3(1), 274-279.
[13]
Anandarajagopal, K.; Tiwari, R.N.; Bothara, K.G.; Sunilson, A.J.; Dineshkumar, C.; Promwichit, P. 2-Mercaptobenzimidazole derivatives: Synthesis and anticonvulsant activity. Adv. Appl. Sci. Res., 2010, 1(2), 132-138.
[14]
Moldovan, Z.; Alexandrescu, L. 2-Mercaptobenzimidazole used as antioxidant in polymeric materials, estimation by derivative spectrophotometry. Acta Chim. Slov., 2002, 49, 909-916.
[15]
Kaur, P.; Wakode, S.R. Antimicrobial properties of benzimidazole and mannich bases of benzimidazole: A review. I.J.S.R.,2014, 5(3), 762-772.
[16]
Yaseen, G.; Sudhakar, J. Design, synthesis and antimicrobial activity of 2-mercaptobenzimidazole derivatives. Int. J. Pharma Bio Sci., 2010, 1(4), 65-68.
[17]
Kaplancikli, Z.A.; Turan-Zitouni, G.; Revial, G.; Guven, K. Synthesis and study of antibacterial and antifungal activities of novel 2-[[(benzoxazole/benzimidazole-2-yl)sulfanyl]acetylamino] thiazoles. Arch. Pharm. Res., 2004, 27(11), 1081-1085.
[18]
Turan-Zitouni, G.; Kaplancikli, Z.A.; Ozdemir, A.; Revial, G.; Guven, K. Synthesis and antimicrobial activity of some 2-(benzo[d]oxazol/benzo[d]imidazol-2-ylthio)-N-(9H-fluoren-9-yl) acetamide derivatives. Phosphorus Sulfur Silicon, 2007, 182, 639-646.
[19]
Tahlan, S.; Kumar, P.; Ramasamy, K.; Mani, V.; Mishra, R.K.; Majeed, A.B.A.; Narasimhan, B. Synthesis, antimicrobial, anticancer evaluation and QSAR studies of N′-substituted benzylidene/ 2-hydroxynaphthalen-1ylmethylene/3-phenyl allylidene/5-oxopen-tylidene-4-(2-oxo-2-(4H-1,2,4-triazol-4-yl) methylamino)benzo-hydrazides. Arab. J. Chem., 2017, 10, S2009-S2017.
[20]
Cappuccino, J.G.; Sherman, N. In microbiology-a laboratory manual. 4th Ed.; Addison Wesley Longman, Inc, California: 263, 1999.
[21]
Pharmacopoeia of India, vol I, Controller of publication, Ministry of health department, Govt. of India, New Delhi, 2007, pp. 37.
[22]
Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J.T.; Bokesch, H.; Kenney, S.; Boyd, M.R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 1990, 82, 1107-1112.


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 19
ISSUE: 13
Year: 2019
Published on: 20 August, 2019
Page: [1080 - 1092]
Pages: 13
DOI: 10.2174/1389557518666181009151008
Price: $65

Article Metrics

PDF: 20
HTML: 4