Abstract
Here in we report the number of strategies for the synthesis of differently substituted benzimidazole derivatives. The protocols involved in the syntheses of these derivatives were one-pot or multi-component. The characterization studies of these derivatives were carried by using different spectroscopic techniques (1H NMR, 13C NMR and MS) and elemental analyses. The biological screening studies revealed that these benzimidazole derivatives show potential antibacterial as well as antifungal behavior. These benzimidazole derivatives not only depicted potential antiulcer properties but also showed moderate to good anticancer/cytotoxic behavior against different cancer cell lines.
Keywords: Benzimidazoles, antimicrobial, antiulcer, anticancer, Escherichia coli, Pseudomonas aeruginosa.
Graphical Abstract
[1]
Grimmet, M.R.; Katritzy, A.R.C.; Rees, W. Imidazole and their Benzoderivative synthesis and Application. Hetero Chem., 1984, 45(5), 457.
[2]
Fairley, T.A.; Tidwell, R.R.; Naiman, D.I.; Corey, M.J. Structure DNA minor Groove Binding and base pair specificity of alkyl-aryl- linked Bis(amidinobenzimidazoles) and Bis(amidinoindoles). Med. Chem., 1993, 36(12), 1746-1753.
[3]
Czarny, A.; Wilson, W.D.; Boykin, D.W. Synthesis of mono-cationic and dicationic analogs of hoescht 33258. J. Heterocycl. Chem., 1996, 33(1), 1393.
[4]
Raut, C.N.; Mane, R.B.; Bangul, S.M.; Janroa, R.A.; Mahulikar, P. Microwave assisted synthesis of 2-(aryl acetylene) Pyridine-1H-benzimidazole derivatives via Sonogashira Coupling. Arkivoc XIV, 2009, 10(1), 5-14.
[5]
Hisano, T.; Ichikawa, M.; Tsumoto, K.; Tasaki, M. Synthesis of benzoxazoles, benzothiazoles and benzimidazoles and evaluation of their antifungal, insecticidal and herbicidal activities. Chem. Pharm. Bull., 1982, 30(8), 2996-3004.
[6]
Reddy, G.V.; Rao, V.R.; Narsaiah, B.; Rao, P.S. A simple and efficient methods for the synthesis of novel trifluoro Benzimidazoles under Microwave irradiation condition. Synth. Commun., 2002, 32(1), 2467-2476.
[7]
Chakrabarty, M.; Karmakar, S.; Mukherji, A.; Arima, S.; Harigaya, Y. Application of sulfanic acid as an eco friendly catalyst in an expedient synthesis of Benzimidazoles. Heterocycles, 2006, 68(1), 967.
[8]
Lin, S.; Yangl, A. Simple and efficient for the synthesis of benzimidazole using air as oxidant. Tetrahedron Lett., 2005, 46(25), 4315-4319.
[9]
Selvan, P.; Radhika, T.P.P.; Janagarag, S.; Kumar, A.S. Synthesis of Novel2-substituted benzimidazoles as potential antimicrobial agents. Res. Biotechnol., 2011, 2(3), 56-57.
[10]
Rao, K.G.; Chakraborty, D. Synthesis,Characterisation and Antibacterial evaluation of some potent 2- substituted benzimidazoles Analogs. Intl. J. Pharm. Sci. Drug Res., 2014, 6(1), 67-69.
[11]
Ahmadi, A. Synthesis, characterisation and antibacterial evaluation of some noval derivatives of 2-bromomethyl benzimidazoles. Bull. Chem. Soc. Ethop., 2014, 28(3), 451-456.
[12]
Koronkwo, A.E.; Owelabi, B.J. Synthesis, characterization and anti-microbial activities of Mercapto benzimidazoles, thiosemicarbizides and thiocyanate mixed ligands Co (II) complexes. J. Res. Sci., 2013, 36(5), 156-162.
[13]
Ahmadi, A.; Niknafs, B.N. Synthesis, characterization of some novel benzimidazole derivatives of 1-Bromo-2,4dinitrobenzene and their antifungal activities. J. Appl. Chem. Res., 2013, 7(4), 85-91.
[15]
Jain, P.; Jain, V.; Jain, K.; Sangam, P.K. Synthesis, antimicrobial activity chemotherapentic potential some novel benzimidazole. Int. J. Drug Design Discov., 1999, 2(4), 43-47.
[16]
Ansari, K.F.; Lal, C.; Khitoliya, R.K. Synthesis and biological activity of some triazole bearing benzimidazole derivative. J. Serb. Chem. Soc., 2011, 76(3), 341-352.
[17]
Hernandez-luis, F.; Compos-Rafael, A.H.; Gabrill, C.; Vazquez, N.; Molia, L.Y. Synthesis and biological activity of 2-(trifluoromethyl)-iH-benzimidazole derivative against some protozoa and trichinella, spiral. Eur. J. Med. Chem., 2010, 41(7), 3135-3141.
[18]
Sharma, S.; Sharma, M.C.; Kohli, D.V. Design, synthesis and pharmacological investigation of some benzimidazole derivatives 4-(5,6-substituted-2-trifluoromethyl-benzimidazole-1-ylmethyl)-antihepertensive agents. J. Optoelectron. Biomed., 2010, 4(1), 203-211.
[19]
Mishra, A.K.; Gautam, V.; Gautam, A.; Bensal, R.; Bensal, I.; Kumar, S.; Gupta, V. Synthesis and antimicrobial activity of some newer benzimidazole derivatives -An overview. J. Pharm. Res., 2010, 3(2), 371-378.
[20]
Subrahmanyam, C.H.S.; Narayan, S. International. J. App. Bio. Pharm. Tech., 2010, 1(2), 689-794.
[21]
Diao, X.; Wang, Y.; Jiang, Y.; Ma, D. Assembly of substituted 1H-benzimidazoles and 1,3-dihhdrobenzimidazole-2-one via CuI/I-Proline catalysed coupling of aqeous Ammonia with2- Iodoacetanilides and 2- Iodo phenyl carbamates. J. Org. Chem., 2009, 74(20), 7974-7977.
[22]
Saha, P.; Raman, T.; Purkait, N.; Ali, M.A.; Paul, R.; Punniyamurthy, T. Ligand -free copper catalyzed synthesis of substituted benzimidazole, 2-Aminobenzimidazole -2-aminobenothiazoles and benzoaxzoles. J. Org. Chem., 2009, 74(35), 8719-8725.
[23]
She, J.; Jiang, Z.; Wang, Y. One-pot synthesis of functionalized benzimidazoles and 1H- pyrimidines via cascade reactions of O-aminoanilines and napthalenes-1,8-diamine with alkynes and p-tolysulfuryl azides. Synletter, 2009, 12(1), 2023-2027.
[24]
Sluiter, J.; Christoffers, J. Synthesis of 1-methlybenzimidazole from carbonitriles. Synletter, 2009, 12(2), 63-66.
[25]
Thakuri, H.; Das, G. One pot synthesis of functionalised benzimidazoles. Arkivoc (XV), 2008, 5(12), 321-328.
[26]
Patil, D.N.; Chatervedi, S.C.; Kakade, D.L.; Dahikar, S.B. Synthesis and antimicrobial activity of some benzimidazoles derivatives. Continent. J. Pharm. Sci., 2008, 2(1), 44-48.
[27]
Ibrahim, H.K.; E.I., Tamany S.H.; Shaarawy, R.I.E.; Ibrahim, M.; Deen, E. Synthesis and investigation of mass spectra of benzimidazole derivatives. Macedon. J. Chem. Engineer., 2008, 27(1), 65-79.
[28]
Niknam, K.; Fatehi-Razvi, A. Synthesis of 2-substituted benzimidazoles by microwave in the presence of Alumina-methane sulfonic acid. J. Iran. Chem. Soc, 2007, 4(4), 438-443.
[29]
Xiangmng, H.; Huiqiang, M.; Yalu, W. P-TsOH cataysed synthesis of 2-aryl substituted benzimidazoles. Arkivoc (XIII), 2007, 37(1), 150-154.
[30]
Alan, A.S.; Gunes, H.S.; Topcu, Z. 1H-benzimidazole derivatives as mammalian DNA Topisomerase I inhibitors. Acta Biochemica Polonica., 2009, 54(3), 561-565.
[31]
Bahrami, K.; Khodaei, M.M.; Kavianinia, I. A simple and efficient one pot synthesis of 2-substitued benzimidazole. Synthesis, 2007, 417-427.
[32]
Du, L-H.; Wang, Y.G. A rapid and efficient synthesis of benzimidazole using hypervalent iodine as oxidant. Synthesis, 2007, 675-678.
[33]
Teawari, A.K.; Mishra, A. Synthesis and antiviral activities of N-substituted-2-substituted benzimidazole derivatives. Indian J. Chem., 2006, 45B, 489-493.
[34]
Jat., R.K. Jat. J.; Pathak. D.P. Benzimidazole Derivatives as Potential Antimicrobial and Antiulcer Agents: A Mini Review. Eur. J. Chem., 2009, 3(15), 2435-2440.
[35]
Rahul, R.; Devanand, N.; Shinde, B. TiCl4 promoted synthesis of benzimidazole derivatives. Indian J. Chem., 2006, 46B, 349-351.
[36]
Ryabukhin, S.V.; Plaskon, A.S.; Volochnykuk, D.M.; Tolmachev, A.A. Synthesis of fused imidazoles from aromatic ortho- diamines or ortho-aminophenol and aldehydes promoted by chlorotrimethylene. Synthesis, 2006, 3715-3726.
[37]
Yang, D.; Fokas, D.; Li, J. Yu; Baldino, C.M. A versatile method for the synthesis of benzimidazole from o-nitroaniline and aldehydes in one step via a reductive cyclisation. Synthesis, 2005, 47-56.
[38]
Reddy, G.; Hedge, P.P.; Ranjan, P.C. Synthesis and biological evaluation of cinitapride related derivatives as potential prokinetic agents. Het. Comm, 2005, 11(1), 23-28.
[39]
Riyabakhin, S.V.; Paskin, A.S.; Dritriy, V. Chlorotrimethylsilane mediated synthesis of functionalized 2-(2hydroxybenzyl) pyrido(1,2a)benzimidazoles. Synthesis, 2007, 1(20), 3155-3162.
[40]
Keiji, K.; Fumihiko, S. Benzimiazole compounds, process for producing the same and use thereof. World Patent No 2002, 030920.
[41]
Cotton, H.; Elebring, T.; Larson, M. LI, L. Asymmetric synthesis of esomprazole. Tetrahedron, 2000, 11(1), 3819-3825.
[42]
Lohray, B.B.; Lohray, V.B.; Kommireddi, G.P. Benzimidazole derivatives as Antiulcer agents. Process for their US Patent No. 6051570, 2000.
[43]
Lopez-Redriguez, M.L.; Benhamu, B.; Morillica, M.J.; Orensaz, I.; Alfaro, M.J.; Martin, I. Benzimidazole derivatives part1: Synthesis and structure-activity relationship of new benzimidazole-4-carboxamides and carboxylate as potent and selective5-HT4 receptor Antogonists. J. Med. Chem., 1999, 42, 5020-5028.
[44]
Nakano, H.; Inoue, T.; Kawasaki, N.; Miyataka, H.; Matsumoto, H.; Taguchi, T.; Inagaki, N.; Nagai, H.; Satoh, T. Synthesis of benzimidazole derivative as anti-allergic agent with 5-lipoxygenase inhibiting action. Chem. Pharm. Bull., 1999, 47(11), 1573-1578.
[46]
Martin, T.L.; Alquier, T.; Asakura, K.; Furukawa, N.; Preitner, F.; Kahn, B.B. Diet-induced obesity alters AMP Kinase activity in hypothalamus and skeletal muscle. J. Biol. Chem., 2006, 281(1), 18933.
[47]
Yu, C.; Chen, Y.; Cline, G.W.; Zhang, D.; Zong, H.; Wang, Y.; Bergeron, R.; Kim, J.K. Cushman, S.W.; Cooney, G.J.; Atcheson, B.; White, M.F.; Kraegen, E.W.; Shulman, G.I. Mechanism by which fatty acid inhibit Insulin activation of IRS-1 Associated phosphatidylinositol3-kinase activity in muscles. J. Biol. Chem., 2002, 277(1), 50230.
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