SYNTHESIS, CHARACTERIZATION AND ANTIBACTERIAL EVALUATION OF SOME POTENT 2-SUBSTITUTED BENZIMIDAZOLE ANALOGUES
Abstract
Present study circumspects synthesis of some novel 2-substituted analogues of Benzimidazole and their spectral characterization by means of UV, IR and 1H NMR. The compounds were screened for antibacterial activity against standard strains of both Gram positive and Gram negative bacteria. Results obtained establish compounds KD1 and KD2 to be significantly responsive against different bacterial strains and as such these compounds can pave the way for development of potent antibacterial agents.
Keywords:
Benzimidazoles, o-phenylenediamine, Antibacterial, Cup-plate methodDOI
https://doi.org/10.25004/IJPSDR.2014.060111References
1. Ansari KF, Lal C. Synthesis, physicochemical properties and anti-microbial activity of some new benzimidazole derivatives. Eur. J. Med. Chem. 2009; 44: 4028-4033.
2. Grocer H, Kus C, Boykin DW, Yildiz S, Altanlar N. Synthesis and Anti-fungal Properties of Some Benzimidazole Derivatives. Bioorg. Med. Chem. 2002; 10: 2589-2596.
3. 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: 185-195.
4. Starcevic K, Kraji M, Ester K, Sabol I, grce M, Pavelic K, Karminskizamola G. Synthesis, antiviral and antitumor activity of 2-substituted-5-amidino-benzimidazoles. Bioorg Med Chem. 2007; 15(13): 4419.
5. Kubo K, Inada Y, Kohara Y, Sugiura Y, Ojima M, Itoh K, Furukawa Y, Nishikawa YK, Naka T. Nonpeptide angiotensin II receptor antagonists. Synthesis and biological activity of benzimidazoles. J Med. Chem. 1993; 36(12): 1772-84.
6. Dubay R, Abuzar S, Sharma S, Chatterjee RK, Katiyar JC. Synthesis and anthelmintic activity of 5(6)-(benzimidazol-2-ylcarbamoyl) and (4-substituted piperazin-1-yl)benzimidazoles. J Med Chem. 1985; 28(11): 1748-50.
7. Mavrova AT, Denkova PS, Tsenov YA, Anichina KK, Vutchev DL. Synthesis and antitrichinellosis activity of some bis(benzimidazol-2-yl)amines. Bioorg Med Chem. 2007; 15(18): 6291-97.
8. Ravina E , Sanchez-Alonso R, Fueyo J, Baltar MP, Bos J, Iglesias R, Sanmartin ML. Synthesis and potential anthelmintic activity of methyl-5-(4-salicyloyl-piperazin-1-yl)-benzimidazole-2-carbamates. Arzneimittelforschung. 1993; 43(6): 689-94.
9. Navarette Vazquez G, Cedilla R, Hernandez Campos A, Yepez A, Hernandez luis F, Valdez J, Morels R, Cortes R , Hernandez M, Castillo R. Synthesis and antiparasitic activity of 2-(trifluoromethyl)-benzimidazole derivatives. Bioorg Med Chem Lett. 2001; 11: 187-90.
10. Katiyar SK, Gordon VR, Mc Laughlin GL, Edlind TD. Antiprotozoal activities of benzimidazoles and correlations with beta-tubulin sequence. Antimicrob Agents Chemother. 1994; 38(9): 2086-90.
11. Goker H, Kus C, Boykin DW, Yildiz S, Altanlar N. Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against Candida species. Bioorg Med Chem. 2002; 10(8):2589-96.
12. Goker H, Ozden S, Yildiz S, Boykin DW. Synthesis and potent antibacterial activity against MRSA of some novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5-carboxamidines. Eur J Med Chem. 2005; 40(10): 1062-69.
13. Desai KG, Desai KR. Green route for the heterocyclization of 2-mercaptobenzimidazole into beta-lactum segment derivatives containing -CONH- bridge with benzimidazole: Screening in vitro antimicrobial activity with various microorganisms. Bioorg Med Chem. 2006; 14(24): 8271-79.
14. Kazimierczuk Z, Upcroft JA, Upcroft P, Gorska A, Starosciak B, Laudy A. Synthesis, antiprotozoal and antibacterial activity of nitro- and halogeno-substituted benzimidazole derivatives. Acta Biochim Pol. 2002; 49(1): 185-95.
15. Mohammad BG, Hussien MA, Abdel-Alim AA, Hashem M. Synthesis and antimicrobial activity of some new 1-alkyl-2-alkylthio-1,2,4-triazolobenzimidazole derivatives. Arch Pharm Res. 2006; 29(1): 26-33.
16. Pawar NS, Dalal DS, Shimpi SR, Mahulikar PP. Studies of antimicrobial activity of N-alkyl and N-acyl 2-(4-thiazolyl)-1H-benzimidazoles. Eur J Pharm Sci. 2004; 21: 115-18.
17. Kus C, Ayhan-Kilcigil G, Can Eke B, Iscan N. Synthesis and antioxidant properties of some novel benzimidazole derivatives on lipid peroxidation in the rat liver. Arch Pharm Res. 2004; 27(2): 156-63.
18. Ates-Alagoz A, Kus C, Coban T. Synthesis and antioxidant properties of novel benzimidazoles containing substituted indole or 1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene fragments. J Enzyme Inhib Med Chem. 2005; 20(4): 325-31.
19. Lazer ES, Matteo MR, Possanza GJ. Benzimidazole derivatives with atypical antiinflammatory activity. J Med Chem. 1987; 30(4): 726-29.
20. Lackner TE, Clissold SP. Bifonazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses. Drugs. 1989; 38(2): 204-25.
21. Ito K, Kagaya H, Fukuda E, Yoshino K, Nose T. Pharmacological studies of a new non-steroidal antiinflammatory drug: 2-(5-ethylpyridin-2-yl)benzimidazole (KB-1043) Arzneimittelforschung. 1982; 32(1) :49-55.
22. Grimmet M R in (eds) Katritzky A R C W Rees. Hetero.chem. 1984; 457
23. Furniss BS, Hannaford AJ, Peter WG, Smith Tetchell AR. Vogel’s Text book of Practical Organic Chemistry, 1989.
24. Ansari KF, Lal C. Synthesis and Biological Activity of Some Heterocyclic Compounds containing Benzimidazole and β-lactam Moiety. J Chem Sci. 2009; 121(6):1017-1025,
25. Hawkey PM, Lewis DA. Medical bacteriology-a practical approach, Oxford University press, 1994.
2. Grocer H, Kus C, Boykin DW, Yildiz S, Altanlar N. Synthesis and Anti-fungal Properties of Some Benzimidazole Derivatives. Bioorg. Med. Chem. 2002; 10: 2589-2596.
3. 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: 185-195.
4. Starcevic K, Kraji M, Ester K, Sabol I, grce M, Pavelic K, Karminskizamola G. Synthesis, antiviral and antitumor activity of 2-substituted-5-amidino-benzimidazoles. Bioorg Med Chem. 2007; 15(13): 4419.
5. Kubo K, Inada Y, Kohara Y, Sugiura Y, Ojima M, Itoh K, Furukawa Y, Nishikawa YK, Naka T. Nonpeptide angiotensin II receptor antagonists. Synthesis and biological activity of benzimidazoles. J Med. Chem. 1993; 36(12): 1772-84.
6. Dubay R, Abuzar S, Sharma S, Chatterjee RK, Katiyar JC. Synthesis and anthelmintic activity of 5(6)-(benzimidazol-2-ylcarbamoyl) and (4-substituted piperazin-1-yl)benzimidazoles. J Med Chem. 1985; 28(11): 1748-50.
7. Mavrova AT, Denkova PS, Tsenov YA, Anichina KK, Vutchev DL. Synthesis and antitrichinellosis activity of some bis(benzimidazol-2-yl)amines. Bioorg Med Chem. 2007; 15(18): 6291-97.
8. Ravina E , Sanchez-Alonso R, Fueyo J, Baltar MP, Bos J, Iglesias R, Sanmartin ML. Synthesis and potential anthelmintic activity of methyl-5-(4-salicyloyl-piperazin-1-yl)-benzimidazole-2-carbamates. Arzneimittelforschung. 1993; 43(6): 689-94.
9. Navarette Vazquez G, Cedilla R, Hernandez Campos A, Yepez A, Hernandez luis F, Valdez J, Morels R, Cortes R , Hernandez M, Castillo R. Synthesis and antiparasitic activity of 2-(trifluoromethyl)-benzimidazole derivatives. Bioorg Med Chem Lett. 2001; 11: 187-90.
10. Katiyar SK, Gordon VR, Mc Laughlin GL, Edlind TD. Antiprotozoal activities of benzimidazoles and correlations with beta-tubulin sequence. Antimicrob Agents Chemother. 1994; 38(9): 2086-90.
11. Goker H, Kus C, Boykin DW, Yildiz S, Altanlar N. Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against Candida species. Bioorg Med Chem. 2002; 10(8):2589-96.
12. Goker H, Ozden S, Yildiz S, Boykin DW. Synthesis and potent antibacterial activity against MRSA of some novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5-carboxamidines. Eur J Med Chem. 2005; 40(10): 1062-69.
13. Desai KG, Desai KR. Green route for the heterocyclization of 2-mercaptobenzimidazole into beta-lactum segment derivatives containing -CONH- bridge with benzimidazole: Screening in vitro antimicrobial activity with various microorganisms. Bioorg Med Chem. 2006; 14(24): 8271-79.
14. Kazimierczuk Z, Upcroft JA, Upcroft P, Gorska A, Starosciak B, Laudy A. Synthesis, antiprotozoal and antibacterial activity of nitro- and halogeno-substituted benzimidazole derivatives. Acta Biochim Pol. 2002; 49(1): 185-95.
15. Mohammad BG, Hussien MA, Abdel-Alim AA, Hashem M. Synthesis and antimicrobial activity of some new 1-alkyl-2-alkylthio-1,2,4-triazolobenzimidazole derivatives. Arch Pharm Res. 2006; 29(1): 26-33.
16. Pawar NS, Dalal DS, Shimpi SR, Mahulikar PP. Studies of antimicrobial activity of N-alkyl and N-acyl 2-(4-thiazolyl)-1H-benzimidazoles. Eur J Pharm Sci. 2004; 21: 115-18.
17. Kus C, Ayhan-Kilcigil G, Can Eke B, Iscan N. Synthesis and antioxidant properties of some novel benzimidazole derivatives on lipid peroxidation in the rat liver. Arch Pharm Res. 2004; 27(2): 156-63.
18. Ates-Alagoz A, Kus C, Coban T. Synthesis and antioxidant properties of novel benzimidazoles containing substituted indole or 1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene fragments. J Enzyme Inhib Med Chem. 2005; 20(4): 325-31.
19. Lazer ES, Matteo MR, Possanza GJ. Benzimidazole derivatives with atypical antiinflammatory activity. J Med Chem. 1987; 30(4): 726-29.
20. Lackner TE, Clissold SP. Bifonazole. A review of its antimicrobial activity and therapeutic use in superficial mycoses. Drugs. 1989; 38(2): 204-25.
21. Ito K, Kagaya H, Fukuda E, Yoshino K, Nose T. Pharmacological studies of a new non-steroidal antiinflammatory drug: 2-(5-ethylpyridin-2-yl)benzimidazole (KB-1043) Arzneimittelforschung. 1982; 32(1) :49-55.
22. Grimmet M R in (eds) Katritzky A R C W Rees. Hetero.chem. 1984; 457
23. Furniss BS, Hannaford AJ, Peter WG, Smith Tetchell AR. Vogel’s Text book of Practical Organic Chemistry, 1989.
24. Ansari KF, Lal C. Synthesis and Biological Activity of Some Heterocyclic Compounds containing Benzimidazole and β-lactam Moiety. J Chem Sci. 2009; 121(6):1017-1025,
25. Hawkey PM, Lewis DA. Medical bacteriology-a practical approach, Oxford University press, 1994.
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01-01-2014
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“SYNTHESIS, CHARACTERIZATION AND ANTIBACTERIAL EVALUATION OF SOME POTENT 2-SUBSTITUTED BENZIMIDAZOLE ANALOGUES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 6, no. 1, Jan. 2014, pp. 67-69, https://doi.org/10.25004/IJPSDR.2014.060111.
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How to Cite
“SYNTHESIS, CHARACTERIZATION AND ANTIBACTERIAL EVALUATION OF SOME POTENT 2-SUBSTITUTED BENZIMIDAZOLE ANALOGUES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 6, no. 1, Jan. 2014, pp. 67-69, https://doi.org/10.25004/IJPSDR.2014.060111.
