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Current Drug Discovery Technologies

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ISSN (Print): 1570-1638
ISSN (Online): 1875-6220

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Research Article

Synthesis, Characterization and Antimicrobial Evaluation of Some N-Substituted Benzimidazole Derivatives

Author(s): Anuj Kumar, Yogesh Kumar, Jagdish K. Sahu* and Sushil Kumar

Volume 17, Issue 1, 2020

Page: [87 - 91] Pages: 5

DOI: 10.2174/1570163815666180831164149

Price: $65

Abstract

Background: Due to the appearance of communicable microbial diseases and the toxicity related with presently used several antimicrobials such as β-lactam antibiotics, tetracyclines, quinolones, macrolides, glycopeptides (vancomycin) etc, demand for new antimicrobial agents has become a great concern in new technologies to improve efficacy and safety.

Methods: In search of new antimicrobial agents with higher potency, some N-substituted benzimidazole derivatives (4, 5a-5h & 6) were obtained by chloroacetylation of benzimidazole followed by reaction with different amines, which were characterized by spectroscopic methods. All the target compounds were evaluated for their antibacterial and antifungal activity against microorganisms using two-fold serial dilution method.

Results: Among the compounds evaluated, compounds 4 and 5d exhibited potent activity against Bacillus thuringiensis and Candida albicans while showed moderate activity against Escherischia coli when compared to amoxicillin and fluconazole. Compound 5a showed significant activity against tested microorganisms.

Conclusion: From the current study, it may be concluded that synthesized compounds are fulfilling in terms of their structural distinctiveness and marked biological properties. These compounds might be encouraged to initiate a new class of antimicrobial agents.

Keywords: Benzimidazoles, antibacterial, antifungal, two-fold serial dilution method, amines, microbial diseases.

Graphical Abstract

[1]
He Y, Wu B, Yang J, et al. 2-piperidin-4-yl-benzimidazoles with broad spectrum antibacterial activities. Bioorg Med Chem Lett 2003; 13(19): 3253-6.
[http://dx.doi.org/10.1016/S0960-894X(03)00661-9] [PMID: 12951103]
[2]
Metwally KA, Abdel-Aziz LM. Lashine el SM, Husseiny MI, Badawy RH. Hydrazones of 2-aryl- -4- carboxylic acid hydrazides: synthesis and preliminary evaluation as antimicrobial agents. Bioorg Med Chem 2006; 14(24): 8675-82.
[http://dx.doi.org/10.1016/j.bmc.2006.08.022] [PMID: 16949294]
[3]
Spasov A, Yozhitsa L, Bugaeva I, Anisimova VA. Benzimidazole derivatives: Spectrum of pharmacological activity and toxicological properties. Pharm Chem J 1999; 33(5): 232-43.
[http://dx.doi.org/10.1007/BF02510042]
[4]
Arjmand F, Mohani B, Ahmad S. Synthesis, antibacterial, antifungal activity and interaction of CT-DNA with a new benzimidazole derived Cu(II) complex. Eur J Med Chem 2005; 40(11): 1103-10.
[http://dx.doi.org/10.1016/j.ejmech.2005.05.005] [PMID: 16006016]
[5]
Barker HA, Smyth RD, Weissbach H, Toohey JI, Ladd JN, Volcani BE. Isolation and properties of crystalline cobamide coenzymes containing benzimidazole or 5, 6-dimethylbenzimidazole. J Biol Chem 1960; 235(2): 480-8.
[PMID: 13796809]
[6]
Ansari KF, Lal C. Synthesis, physicochemical properties and antimicrobial activity of some new benzimidazole derivatives. Eur J Med Chem 2009; 44(10): 4028-33.
[http://dx.doi.org/10.1016/j.ejmech.2009.04.037] [PMID: 19482384]
[7]
Ansari KF, Lal C. Synthesis and evaluation of some new benzimidazole derivatives as potential antimicrobial agents. Eur J Med Chem 2009; 44(5): 2294-9.
[http://dx.doi.org/10.1016/j.ejmech.2008.01.022] [PMID: 18316140]
[8]
Küçükbay H, Durmaz R, Orhan E, Günal S. Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds. Farmaco 2003; 58(6): 431-7.
[http://dx.doi.org/10.1016/S0014-827X(03)00068-5] [PMID: 12767382]
[9]
Güven OO, Erdoğan T, Göker H, Yildiz S. Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers. Bioorg Med Chem Lett 2007; 17(8): 2233-6.
[http://dx.doi.org/10.1016/j.bmcl.2007.01.061] [PMID: 17289382]
[10]
Sharma D, Narasimhan B, Kumar P, Jalbout A. Synthesis and QSAR evaluation of 2-(substituted phenyl)-1H-benzimidazoles and [2-(substituted phenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanones. Eur J Med Chem 2009; 44(3): 1119-27.
[http://dx.doi.org/10.1016/j.ejmech.2008.06.009] [PMID: 18657885]
[11]
Grocer H, Kus C, Boykin DW, Yildiz S, Altanlar N. Synthesis and anti-fungal properties of some benzimidazole derivatives. Bioorg Med Chem 2002; 10: 2589-96.
[12]
Kazimierczuk Z, Upcroft JA, Upcroft P, Gorska A, Starosciak B, Laudy A. Synthesis and antiproto-zoal activity of some 2-(trifluoromethyl)-1H-benzimidazole bioisosteres. Acta Biochim Pol 2002; 49: 185-95.
[http://dx.doi.org/10.18388/abp.2002_3835] [PMID: 12136939]
[13]
Patil A, Ganguly S, Surana SA. systemic review of benzimidazole derivatives as an antiulcer agent. Rasayan J Chem 2008; 1(3): 447-60.
[14]
Tunçbilek M, Kiper T, Altanlar N. Synthesis and in vitro antimicrobial activity of some novel substituted benzimidazole derivatives having potent activity against MRSA. Eur J Med Chem 2009; 44(3): 1024-33.
[http://dx.doi.org/10.1016/j.ejmech.2008.06.026] [PMID: 18718694]
[15]
Haugwitz RD. Anti-parasitic agents Synthesis and anti-helmintic activities of novel 2-substituted isothiocya-natobenzoxazoles and benzimidazole. J Med Chem 1982; 25: 969-74.
[http://dx.doi.org/10.1021/jm00350a017] [PMID: 7120286]
[16]
Villanova PA. NCCLS: Method for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. 5th ed. NCCLS 2000; Approved standard M7: p. A5

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