Synthesis of some novel benzimidazole derivatives and their biological evaluation

Dnyandev Radhu Gund; Balivada Venkata Satyasai Varaprasad Rao; Pandurang Narayanrao Mandhare; Sanjay Dashrath Vaidya

doi:10.5155/eurjchem.6.3.270-274.1242

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Published: Sep 30, 2015

DOI: https://doi.org/10.5155/eurjchem.6.3.270-274.1242

Keywords:

Alkylation, Benzimidazole, Suzuki coupling, Antifungal activity, Phenyl boronic acid, Antibacterial activity

Section

Research Article

Issue

Vol. 6 No. 3 (2015): September 2015

Dates

Received 2015-01-11
Accepted 2015-04-05
Published 2015-09-30

Dnyandev Radhu Gund

Department of Chemistry, Jagdishprasad Jhabarmal Tibrewala University, Jhunjhunu, Rajasthan, 333001, India

Balivada Venkata Satyasai Varaprasad Rao

Department of Chemistry, Pacific University, Udaipur, Rajasthan, 313024, India

Pandurang Narayanrao Mandhare

Department of Chemistry, Shreemati Nathibai Damodar Thackersey Women’s University, Mumbai, 400049, India

Sanjay Dashrath Vaidya

Department of Chemistry, Jagdishprasad Jhabarmal Tibrewala University, Jhunjhunu, Rajasthan, 333001, India

Abstract

A series of novel benzimidazole derivatives have been synthesized by the condensation of o-phenylenediamine with 4-bromophenoxy acetic acid and product obtained was alkylated at the benzimidazole -NH with different electrophilic reagents. Subsequent reactions of the products by the Suzuki Coupling between benzimidazole derivatives and phenylboronic acid derivatives were accomplished. All these compounds were characterized by FT-IR, ¹H NMR, MS and elemental analysis. These compounds were screened for their potential antibacterial and antifungal activities. This exhibited some promising results towards testing organism in-vitro.

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How to Cite

(1)

Gund, D. R.; Rao, B. V. S. V.; Mandhare, P. N.; Vaidya, S. D. Synthesis of Some Novel Benzimidazole Derivatives and Their Biological Evaluation. Eur. J. Chem. 2015, 6, 270-274.

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References

[1]. O'Neil, M. J.; Smith; M.; Heckelman, P. E. The Merck Index, 13th Edition, Merck & Co. Inc., NJ. , Monograph Number: 10074, 2001.

[2]. Nakamura, S.; Tsuno, N.; Yamashita, M.; Kawasaki, I.; Ohta, S.; Ohishi, Y. J. Chem. Soc. Perkin Trans 1, 2001, 429-436
http://dx.doi.org/10.1039/b007560o

[3]. Migawa, M. T.; Gardet, J. L.; Walker, J. A.; Koszalka, G. W.; Chamberlain, S. D.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 1998, 41, 1242-1251.
http://dx.doi.org/10.1021/jm970545c

[4]. Townsend, L. B.; Devivar, R. V.; Turk, S. R.; Nassiri, M. R. Drach, J. C. J. Med. Chem. 1995, 38, 4098-4105.
http://dx.doi.org/10.1021/jm00020a025

[5]. Preston, P. N. Chem. Rev. 1974, 74, 279-314.
http://dx.doi.org/10.1021/cr60289a001

[6]. Hazelton, J. C.; Iddon, B.; Suschitzky, H.; Woolley, L. H. Tetrahedron 1995, 51, 10771-10794.
http://dx.doi.org/10.1016/0040-4020(95)00642-L

[7]. Labaw, C. S.; Webb, R. L. U. S 4285878, 1981; Chem. Abstr. 1981, 95, 168837.

[8]. Meisel, P.; Heidrich, H. J.; Jaensch, H. J.; Kretzschmar, E.; Henker, S.; Laban, G. DD243284, 1987; Chem. Abstr. 1987, 107, 217629.

[9]. Kyle, D.; Goehring, R. R.; Shao, B. WO 001, 039775, Chem. Abstr. 2001, 135, 33477.

[10]. Kuchkguzel, I.; Kucukguzel, G.; Rollas, S.; Kiraz, M. Bioorg. Med. Chem. Lett. 2001, 11, 1703-1708.
http://dx.doi.org/10.1016/S0960-894X(01)00283-9

[11]. Kruse, L. L.; Ladd, D. L.; Harrsch, P. B.; McCabe, F. L.; Mong, S. M.; Faucette, L.; Johnson, R. J. Med. Chem. 1989, 32, 409-417.
http://dx.doi.org/10.1021/jm00122a020

[12]. Islam, I.; Skibo, E. B.; Dorr, R. T.; Alberts, D. S. J. Med. Chem. 1991, 34, 2954-2961.
http://dx.doi.org/10.1021/jm00114a003

[13]. Roth, T.; Morningstar, M. L.; Boyer, P. L.; Hughes, S. H.; Buckheit, R. W.; Michejda C. J. J. Med. Chem. 1997, 40, 4199-4207.
http://dx.doi.org/10.1021/jm970096g

[14]. Destro, M.; Cagnoni, F.; Dognini, G. P.; Galimberti, V.; Taietti, C.; Cavalleri, C.; Galli, E. Expert Opin. Pharmaco. 2011, 12, 2719-2735.
http://dx.doi.org/10.1517/14656566.2011.632367

[15]. Lazer, S. E.; Martha, R.; Matteo, M. R.; Possanza, G. J. J. Med. Chem. 1987, 30, 726-729.
http://dx.doi.org/10.1021/jm00387a026

[16]. Nakano, H, ; Inoue, T.; Kawasaki, N.; Miyataka, H.; Matsumoto, H.; Taguchi, T.; Inagaki, N.; Nagai, H.; Satoh, T. Chem. Pharm. Bull. 1999, 47, 1573-1578.
http://dx.doi.org/10.1248/cpb.47.1573

[17]. Bao, J.; Lan, P.; Lu, H.; Makara, G. M.; Romero, F. A.; Sebhat, L.; Wodka, D.; Dang, Q.; Chung, D. M.; Gibson, T. S.; Jiang, H.; Cashion, D. K.;

[18]. Jain, P.; Sharma, P. K.; Rajak, H.; Pawar, R. P.; Patil, U. K .; Singour, P. K. Arch Pharm. Res. 2010, 33, 971-980.
http://dx.doi.org/10.1007/s12272-010-0701-8

[19]. Alpan, A. S.; Zencir, S.; Zupko, I.; Coban, G.; Rethy, B.; Gunes, H. S.; Topcu, Z. J. Enzym. Inhib. Med. Ch. 2009, 24, 844-849.
http://dx.doi.org/10.1080/14756360802420831

[20]. Vinodkumar, R.; Vaidya, S. D.; Siva Kumar, B. S.; Bhise, U. N.; Mashelkar, U. C. Arkivoc. 2008, 14, 37-49.

[21]. Philips, M. A. J. Chem. Soc. 1928, 2393-2399.
http://dx.doi.org/10.1039/jr9280002393

[22]. Reddy, V. B.; Singla, R. K.; Bhat, G. V.; Shenoy, G. G. Asian J. Res. Chem. 2009, 2, 162-167.

[23]. Gund, D. R.; Vaidya, S. D. Int. Res. J. Pharm. 2014, 5, 348-352.
http://dx.doi.org/10.7897/2230-8407.050473

[24]. Miyaura, A.; Yanagi, T.; Suzuki, A. Synthetic. Commun. 1981, 11, 513-519.
http://dx.doi.org/10.1080/00397918108063618

[25]. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685-4696.
http://dx.doi.org/10.1021/ja042491j

[26]. Kotha, S.; Lahiri, K.; Dhurke, K. Tetrahedron 2002, 58, 9633-9695.
http://dx.doi.org/10.1016/S0040-4020(02)01188-2

[27]. Frankel, S.; Reitman, S.; Sonnenwirth, A. C.; Gradwol's Clinical Laboratory Methods and Diagonosis, C. V. Mosby Company, Germany, 7th edition, 1970, 2, 1406.

[28]. Kempaiah, R. D.; Gowdegowda, C. P. Eur. J. Chem. 2012, 3, 359-362.
http://dx.doi.org/10.5155/eurjchem.3.3.359-362.607

[29]. Khabnadideh, S.; Rezaei, Z.; Pakshir, K.; Zomorodian, K.; Ghafari, N. Res. Pharm. Sci. 2012, 7, 65-72.

[30]. Mueller, J. H.; Hinton, J. Proc. Soc. Exp. Biol. Med. 1941, 48, 330-333.
http://dx.doi.org/10.3181/00379727-48-13311

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Analytical Instrumentation Facility, Punjab University, India

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