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Synthesis and biological activity of some heterocyclic compounds containing benzimidazole and beta-lactam moiety

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Abstract

A number of 1N-substituted-2-methyl benzimidazole derivatives have been synthesized and tested for their antibacterial activities. The chemical structures of the newly synthesized compounds were verified on the basis of spectral and elemental methods of analyses. Investigation of antimicrobial activity of the compounds was done by disc diffusion method using Gram-positive (S. aureus, S. mutans and B. subtilis), Gram-negative (E. coli, S. typhi and P. aeruginosa) bacteria and fungi (C. albicans, A. flavus and A. niger). Among the compounds tested 5a, 5b, 5d, 5i, 5j and 5k exhibited good antibacterial activities against Gram positive bacteria, while 5d and 5i also showed notable antifungal activity. Specially compounds 5a and 5b exhibited appreciable activity against S. aureus and B. subtilis comparable to reference drugs.

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References

  1. Wright J B 1951 Chem. Rev. 48 397

    Article  CAS  Google Scholar 

  2. Preston P N 1974 Chem. Rev. 74 279

    Article  CAS  Google Scholar 

  3. Preston P N 1980 In Benzimidazole and congeneric tricyclic compounds (eds) A Weissberger and E C Taylor (New York: John Wiley and Sons), Part-2, pp. 63–147

    Google Scholar 

  4. Grimmett M R 1984 In Comprehensive heterocyclic chemistry (ed.) K T Pots (Oxford: Pergamon) pp. 345–498

    Google Scholar 

  5. Hoffman K 1953 In Imidazole and its derivatives (ed.) A Weissberger; The chemistry of heterocyclic compounds (New York: Interscience Publishers, Inc) pp. 247–317

    Chapter  Google Scholar 

  6. Kus C, Ayhan-Kilcigil G, Can Eke B and Iscan M 2004 Arch. Pharm. Res. 27 156

    Article  CAS  Google Scholar 

  7. Ates-Alagoz Z, Kus C and Coban T 2005 J. Enzyme Inhib. Med. Chem. 20 325

    Article  CAS  Google Scholar 

  8. Goker H, Kus C, Boykin D W, Yildiz S and Altanlar N 2002 Bioorg. Med. Chem. 10 2589

    Article  CAS  Google Scholar 

  9. Goker H, Ozden S, Yildiz S and Boykin D W 2005 Eur. J. Med. Chem. 40 1062

    Article  Google Scholar 

  10. Desai K G and Desai K R 2006 Bioorg. Med. Chem. 14 8271

    Article  CAS  Google Scholar 

  11. Kazimierczuk Z, Upcroft J A, Upcroft P, Gorska A, Starosciak B and Laudy A 2002 Acta Biochim. Polon. 49 185

    CAS  Google Scholar 

  12. Mohammad B G, Hussien M A, Abdel-Alim A A and Hashem M 2006 Arch. Pharm. Res. 29 26

    Article  Google Scholar 

  13. Pawar N S, Dalal D S, Shimpi S R and Mahulikar P P 2004 Eur. J. Pharm. Sci. 21 115

    Article  CAS  Google Scholar 

  14. Dubey R, Abuzar S, Sharma S, Chatterjee R K and Katiyar J C 1985 J. Med. Chem. 28 1748

    Article  CAS  Google Scholar 

  15. Mavrova A T, Denkova P S, Tsenov Y A, Anichina K K and Vutchev D L 2007 Bioorg. Med. Chem. 15 6291

    Article  CAS  Google Scholar 

  16. Ravina E, Sanchez-Alonso R, Fueyo J, Baltar M P, Bos J, Iglesias R and Sanmartin M L 1993 Arzneim. Forsch. 43 684

    Google Scholar 

  17. Starcevic K, Kralj M, Ester K, Sabol I, Grce M, Pavelic K and Karminski-Zamola G 2007 Bioorg. Med. Chem. 15 4419

    Article  CAS  Google Scholar 

  18. Kubo K, Inada Y, Kohara Y, Sugiura Y, Ojima M, Itoh K, Furukawa Y, Nishikawa Y K and Naka T 1993 J. Med. Chem. 36 1772

    Article  CAS  Google Scholar 

  19. Ram S, Wise D S, Wotring L L, McCall J W and Townsend L B 1992 J. Med. Chem. 35 539

    Article  CAS  Google Scholar 

  20. Lazer E S, Matteo M R and Possanza G J 1987 J. Med. Chem. 30 726

    Article  CAS  Google Scholar 

  21. Lackner T E and Clissold S P 1989 Drugs 38 204

    Article  CAS  Google Scholar 

  22. Ito K, Kagaya H, Fukuda T, Yoshino K and Nose T 1982 Arzneim. Forsch. Drug Res. 32 49

    CAS  Google Scholar 

  23. Navarette-Vazquez G, Cedilla R, Hernandez-Campos A, Yepez A, Hernandez-Luis F, Valdez J, Morales R, Cortes R, Hernandez M and Castillo R 2001 Bioorg. Med. Chem. 11 187

    Article  Google Scholar 

  24. Katiyar S K, Gordon V R, McLaughlin G L and Edlind T D 1994 Antimicrob. Agents Chemother. 38 2986

    Google Scholar 

  25. Li Y F, Wang G F, He P L, Huang W G, Zhu F H, Gao H Y, Tang W, Luo Y, Feng C L, Shi L P, Ren Y D, Lu W and Zuo J P 2006 J. Med. Chem. 49 4790

    Article  CAS  Google Scholar 

  26. Kidwai M, Sapra P and Bhushan K R 1999 Curr. Med. Chem. 6 195

    CAS  Google Scholar 

  27. Deshmukh A R, Bhawal B M, Krishnaswamy D, Govande V V, Shinkre B A and Jayanthi A 2004 Curr. Med. Chem. 11 1889

    CAS  Google Scholar 

  28. Diurno M V, Mazzoni O, Piscopo E and Bolognese A 1992 Il Farmaco 47 239

    CAS  Google Scholar 

  29. Alcaide B and Almendros P 2004 Curr. Med. Chem. 11 1921

    CAS  Google Scholar 

  30. Singh S G and Boycie J M 2005 Il Farmaco 60 727

    Article  CAS  Google Scholar 

  31. Vaccaro W D, Sher R and Jr Davis H R 1998 Bioorg. Med. Chem. Lett. 8 319

    Article  CAS  Google Scholar 

  32. Ansari K F and Lal C 2009 Eur. J. Med. Chem. 44 4028

    Article  CAS  Google Scholar 

  33. Ansari K F and Lal C 2009 Eur. J. Med. Chem. 44 2294

    Article  CAS  Google Scholar 

  34. National Committee for Clinical Laboratory Standards, Performance Standards for Antimicrobial Disk Susceptibility tests; Approved Standard M2-A8, Clinical and Laboratory Standards Institute, Wayne, PA, USA, 2003

    Google Scholar 

  35. Furniss B S, Hannaford A J, Smith P W G and Tatchell A R 1998 Vogel’s text book of practical organic chemistry (England: ELBS Longman) pp. 1162–1163

    Google Scholar 

  36. Registry No. 301684-45-7 (for compound 2)

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  1. Department of Chemistry, Harcourt Butler Technological Institute, Nawabganj, Kanpur, 208 002, India

    K. F. Ansari & C. Lal

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  1. K. F. Ansari
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  2. C. Lal
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Correspondence to C. Lal.

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Ansari, K.F., Lal, C. Synthesis and biological activity of some heterocyclic compounds containing benzimidazole and beta-lactam moiety. J Chem Sci 121, 1017–1025 (2009). https://doi.org/10.1007/s12039-009-0114-8

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  • DOI: https://doi.org/10.1007/s12039-009-0114-8

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