Mannich Bases of 2-Substituted Benzimidazoles - A Review
Keywords:Mannich Bases, Substituted Benzimidazoles, Pharmacological Activities
Mannich bases are the end products of mannich reaction and are known as beta amino ketone carrying compounds. Mannich reaction is a carbon carbon bond forming nucleophilic addition reaction which helps in synthesizing N-methyl derivatives and many other drug molecules. Mannich base derivatives of benzimidazoles possess many pharmacological properties such as anti-oxidant, anti-inflammatory, anticancer, antiviral, anthelmintic and play an important role in medical field. As these drugs are clinically useful in treatment of microbial infections and exhibit other therapeutic activities also, so this encouraged the development of more potent, novel and clinically significant compounds. In this review synthesis and various biological activities of new mannich bases of benzimidazole derivatives reported is discussed.
Aanadhi, M.V., Verma, A.K., Sujatha, R., Kamal Raj, R. (2013) Synthesis and characterization of novel mannich bases of benzimidazole derivatives for antibacterial and antifungal activity. International Journal of Pharmacy and Pharmaceutical Sciences, 5(2) : 295-297.
Afaf, H.E., Fahmy,H.H., Abdelwahed, S.H.A. (2000) Synthesis and antimicrobial properties of some new benzimidazole derivatives.Molecules, 5: 1429-1438. http://dx.doi.org/10.3390/51201429
Anil, R. (2010) Mannich bases of benzimidazole-synthesis and antimicrobial properties.A short review. European J.of Chemistry, 7(1): 222-226.
Ashok, M., Holla, B.S., and Poojary. B. (2007) Convenient one pot synthesis and antimicrobial evaluation of some new Mannich bases carrying 4-methylthiobenzyl moiety. European J. of Medicinal Chemistry, 42(8): 1095-1101. http://dx.doi.org/10.1016/j.ejmech.2007.01.015
Barlin,G.B., and Jiravinya, C. (1990) Potential antimalarials.X.Di-mannich bases of 4-(7’-trifluoromethyl-1’,5’-naphthyridin-4’-ylamino)phenol and N-(4’-Diethylamino-1’- methylbutyl)-7-trifluoromethyl-1,5-naphthyridin-4-amine.Australian J. of Chemistry, 43(7): 1175-1181. http://dx.doi.org/10.1071/CH9901175
Bennet-Jenlins, E., and Baryant, C. (1996) Novel sources of anthelmintics. International J. for Paracitology, 26(8-9) : 937-947. http://dx.doi.org/10.1016/S00207519(96)80068-3
Bhusare,S.R., Pawar,R.P., Vibhute,Y.B. (2001) Synthesis and antibacterial activity of some new 2-(substituted phenyl sulphonamido)-6-substituted benzothiazoles. Indian J.of Heterocyclic Chemistry,11(1): 79-80.
Chakarrarvarthi, K., Gokulakrishnan, K., Suman, T., Tamilvendan, D. (2013) Synthesis,spectral,antimicrobial and antioxidant studies on diamide mannich base derivatives. International Journal of Pharmacy and Pharmaceutical Sciences, 6(1): 492-495.
Cummings, T.F., and Shelton, J.R. (1960) Mannich reaction Mechanisms.Journal of Organic chemistry, (25): 419-423. http://dx.doi.org/10.1021/jo01073a029
Edwards, M.L., Ritter, H.W., Stemeric, D.M., Stewart K.T. (1983) Mannich bases of 4-phenyl3-buten-2-one:a new class of antiherpes agent. J.of Medicinal Chemistry, 26(3): 431-436. http://dx.doi.org/10.1021/jm00357a020
Elarafi, M.G.,Ibrahim, M.N. (2010) Synthesis and spectral studies of mannich bases derived from 2-substituted benzimidazoles. International J. of Chem.Tech.Resr. 4: 2097-2099.
Evans, B.E., Rittle, K.E., Bock, M.G.,Hirshfield J.(1988) Methods for drug discovery, development of potent selective, orally effective cholecystokinin antagonist. J.Med.Chem. 31: 2235-2246 http://dx.doi.org/10.1021/jm00120a002
Gul,H.I., Vepsalainen, J., Gul, M., Erciyas, E. and Hanninen, O. (2000) Cytotoxic activities of mono and bis mannich bases derived from acetophenone against Renca and Jurkat cells. Pharmaceutica Acta Helvetiae, 74(4): 393-398. http://dx.doi.org/10.1016/S0031-6865(00)00022-4
Ivanova, Y., Momekov, G., Petrov, O., Karaivanova, M. and Kalcheva, V. (2007) Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2-(3H)-benzoxazolones.European J.of Medicinal Chemistry, 52(11-12): 1382-1387. http://dx.doi.org/10.1016/j.ejmech.2007.02.019
Jesudason, E.P., Sridhar, S.K., Padma, E.J., Shanmugapandiyan, P., Inayathullah, M., Arul, V., Selvaraj, D., Jayakumar, R. (2009) E.Journal of Medicinal Chemistry, 44: 2307-2312. http://dx.doi.org/10.1016/j.ejmech.2008.03.043
Kalluraya, B., Chimbalkar, R.M. and Hedge, J.C. (2005) Anticonvulsant activity of nicotinyl/ isonicotinyl substituted 1,2,4-triazol-5-thione Mannich bases.Indian Journal of heterocyclic Chemistry, 15(1): 15-18.
Kamlesh, V., Arun, S. (2009) Design docking and synthesis of some 6-benzimidazoyl pyrans and screening of their antitubercular activity. European Journal of Chemistry, 6(1): 281-288.
Kashiyama, E., Hutchinson, I., Chua, M.S. et al. (1999) Antitumour benzothiazoles.8.1 Synthesis,metabolic formation and biological propertie of the C and N oxidation products of antitumour-2-(4-aminophenyl)-benzothiazoles. Journal of Medicinal Chemistry. 42(20): 4172-4184. http://dx.doi.org/10.1021/jm990104o
Koksal, M., Gokhan, N., Kupeli, E., Yesilada,E., Erdogan, H.(2007) Analgesic and antiinflammatory activities of some new mannich bases of 5- nitro-2-benzoxazolinones. Archives of Pharmacal Research, 30(4): 419-424. http://dx.doi.org/10.1007/BF02980214
Kumar, S.V., Subramanian, M.R., Chinnaiyan, S.K. (2013) Synthesis, characterisation and evaluation of N-mannich bases of 2-substituted Benzimidazole derivatives. Journal of Young Pharmacists, 5: 154-159. http://dx.doi.org/10.1016/j.jyp.2013.11.004
Kumar, N., Sharma, C.N., Ranawat, M.S., Singh, H.P., Chauhan, L.S., Dashora, N. (2015) Synthesis, analgesic and anti-inflaammatory activities of novel mannich bases of benzimidazoles. Journal of Pharmaceutical Investigation, 45: 65-71. http://dx.doi.org/10.1007/s40005-014-0145-0
Malinka, W., Swiatek, P., Filipek, B., Sapa, J., Jezierska, A., Koll, A. 2005) Synthesis analgesic activity and computational study of new isothiazolopyridines of mannich base type.Farmaco, 60(11-12): 961-968. http://dx.doi.org/10.1016/j.farmac.2005.08.005
March, J. (1992) Advanced Organic Chemistry: Reaction Mechanisms and Structure, Fourth edition, A Wiley-Interscience Publication, John Wiley and Sons, New York: 900-902.
Mariappan, G., N.R.Bhuyan, N.R., Kumar, P., Kumar, D., K.Murali, K. (2011) Synthesis and biological evaluation of mannich bases of benzimidazole derivatives.Indian Journal of Chemistry, 50 B: 1216-1219.
Mason, J.S., Morize, I., Menard, P.R. (1999) New 4-point pharmacophore method for molecular similarity and diversity applications: Overview of the method and applications including a novel approach to the design of combinatorial libraries containing privileged sub-structures. J.Med. Chem. 42: 3251-3264. http://dx.doi.org/10.1021/jm9806998
Misra, P.S., Shanmugasundaram, P., Chaudhary, R., Anandhi, M.V. (2010) Synthesis of 2-phenyl benzimidazole derivatives and their Schiff bases as possible antimicrobial agents. Rasayan Journal of Chemistry. 3(1): 51-54.
Mohan Rao G, Narsimha Reddy Y, Vijaya Kumar B, Evaluation of analgesic and antiinflammatory activities of N-Mannich bases of substituted 2-mercapto-1-H-benzimidazoles. International J. of Applied Biology and Pharmaceutical Technology, 2013, 4(1),38-46.
Murugesan S., et al. (2011) J. of Pharmacy Research, 498: 2679-2681.
Padmavati, V., Subbaiah, D.R.C.V., Mahesh, K., Lakshmi, T.R. (2007) Synthesis and bioassay of amino-pyrazolone,amino isoxazolone and amino-pyrimidinone derivatives. Chem.Pharm. Bull. 55: 1704-1709. http://dx.doi.org/10.1248/cpb.55.1704
Pandeya, S.N., Sriram, D., Nath,G., and De Clercq, E. (2000) Synthesis , antibacterial, antifungal and anti-HIV activities of norfloxacin mannich bases. European J. of Medicinal Chemistry, 35(2): 249-255. http://dx.doi.org/10.1016/S0223-5234(00)00125-2
Racane, L., Kulenovic, V.T., Jakic, L.E., Boykin, D.W., and Zamola, G.K. (2001) Synthesis of bis substituted amidino-benzothiazoles as potential anti-HIV agents. Heterocycles,
: 2085-2098. http://dx.doi.org/10.3987/COM-01-9305
Reddy B.A (2010) Synthesis,Characterization and biological evaluation of 1,2 disubstituted benzimidazole derivatives using mannich bases.European journal of Chemistry, 7(1): 222-226.
Rita, R., and Shrivastava, P. (2012) Synthesis and Characterization of some N-Mannich bases as potential antimicrobial,anthelmintic and insecticidal agents.Chemical Science Transactions, 1(2) : 431-439. http://dx.doi.org/10.7598/cst2012.184
Saraswathi, M., Rohini, R.M., Nayeem, N. (2010) Synthesis and evaluation of mannich bases of benzimidazo [1,2-c] quinazolin- 6(5h)-thione for antimicrobial activity. Pak.J.of Pharmaceutical Sciences, 23(4): 459-462.
Scott, M.K., Martin, G.E., Distefano, D.L., et al. (1992) Pyrrole Manncih bases as potential antipsychotic agnts. J. of Medicinal chemistry, 35(3): 552-558. http://dx.doi.org/10.1021/jm00081a018
Selvam P., et al. (2010) International J.of Pharmaceutical Sciences and Research, 1(9): 105-119.
Shah, T.B., Gupte, A., Patel,M.R., Patel, H.,Patel, V.C. (2009) Synthesis and in vitro study of biological activity of heterocyclic N-Mannich bases.Indian Journal of Chemistry, 48B: 88-96.
Singh, B.N., Shukla, S.K. (2007) Synthesis and biological activity of sulphadiazine schiff’s bases of isatin and their N-Mannich bases. Asian J. of Chemistry. 19(7): 5013-5018.
Spasov, A.A., Yozhitsa, I.N., Bugaeva L.I.(1999) Benzimidazole derivatives: Spectrum of Pharmacological activity and toxicological properties (a review). Pharm. Chem. Journal, 33:232-243. http://dx.doi.org/10.1007/bf02510042
Thompson, B.B. (1968) The Mannich Reaction, Mechanistic & Technological considerations. J of Pharamaceutical Sciences, 57(5): 715-733. http://dx.doi.org/10.1002/jps.2600570501
Vashishtha, S.C., Zello, G.A., Nienaber K.H., el al (2004) Cytotoxic and anticonvulsant aryloxy aryl mannich bases and related compounds.European Journal of Medicinal Chemistry, 2004, 39(1): 27-35. http://dx.doi.org/10.1016/j.ejmech.2003.09.011
Walia, R., Md Hedaitullah, Naaz, S.F., Iqbal, K., Lamba, H.S. (2011) Benzimidazole DerivativesAn Overview. International Journal of Research in Pharmacy & Chemistry, 1(3): 565-574.
White, A.W., Almassy, R., Calvert,A.H., Golding, B.T. (2000) Resistance modifying agents,Synthesis and Biological properties of Benzimidazole inhibitors of DNA repair enzyme Poly(ADP Ribose) polymerase.Journal of Med.Chem. 43: 4084-4097. http://dx.doi.org/10.1021/jm000950v
Zhu, Z., Lippa, B., Drach, J.C. (2000) Design Synthesis and biological evaluation of tricyclic nucleosides (Dimensional probes) as analogues of certain antiviral polyhalogenated Benzimidazole Ribonucleosides.Journal of Med. Chemistry, 43: http://dx.doi.org/10.1021/jm990290y
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Based on a work at https://jptrm.chitkara.edu.in