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Metal-based Antimicrobial Agents: Synthesis, Characterization and Biological Studies of Mannich Base Derivatives of Benzimidazole and Their Metal Complexes

Received: 28 October 2013    Accepted:     Published: 20 November 2013
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Abstract

Novel Mannich base derivatives of Benzimidazole were prepared through the condensation reaction of benzimidazole derivative with formaldehyde and primary and/ secondary amine. Zinc(II), copper(II), nickel(II) and cobalt(II) complexes of Mannich bases have also been synthesized. All the compounds were fully characterized by, elemental analyses, magnetic moment determination, molar conductivity measurement, thermogravimetric analysis, spectral and analytical data. Experimental results showed that metal complexes act as bi-dentate ligands towards divalent metal ions via azomethine-N and deprotonated-O while suggesting an octahedral geometry. All the compounds were screened for in-vitro antibacterial and antifungal activity against various bacterial and fungal strains. Almost all the compounds showed good potent activity against microorganisms. It was also seen that compounds with complexed form were more active as compared to un-complexed form. The prepared compounds were also screened for their cytotoxicity and results showed that only Ni(II) complexes exhibit some cytotoxicity while all other compounds were almost inactive.

DOI 10.11648/j.sjc.20130105.12
Published in Science Journal of Chemistry (Volume 1, Issue 5, December 2013)
Page(s) 56-66
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Mannich Bases, Benzimidazole, Metal Complexes, Biological Activity, Cytotoxicity

References
[1] X. C. Huang, J. P. Zhang, X. M. Chen, J. Am. Chem. Soc. 126, 2004, 13218-13219.
[2] T. J. Cardwell, A. J. Edwards, R. M. Hartshorn, R. J. Holmes, Aust. J. Chem. 50, 1997, 1009-1015.
[3] Y. P. Tong and S. L. Zheng, J. Mol. Struct. 841, 2007, 34-40.
[4] Y. P. Tong, S.L. Zheng, and X.M. Chen, J. Mol. Struct. 826, 2007, 104-112.
[5] S. Murugesan, S. Sathiyamoorthy, J. Pharm. Res. 4, 2011, 2679-2681.
[6] V. Kamlesh, Patel, and S. Arun, Eur. J. Chem. 6, 2009, 281-288.
[7] B.A. Reddy, Eur. J. Chem. 7, 2010, 222-226.
[8] S. Periyasamy, R.L. Dhani, P. Christophe, Int. J. Pharmaceut. Sci. Res. 1, 2010, 105-109.
[9] E.P. Jesudason, S.K. Sridhar, E.J. Padma, et al., Eur. J. Med. Chem. 44, 2009, 2307-2312.
[10] [M. Arif, M.M.R. Qurashi, M.A. Shad, J. Coord. Chem. 64:11, 2011, 1914-1930.
[11] J. Pragathi, K. Mounika, M. Padmaja, M. Lakshmi, C. Gyanakumari, Eur. J. Chem. 8, 2011, 1662-1669.
[12] Y.S. Chhonker, B. Veenu, S.R. Hasim, et al., Eur. J. Chem. 6, 2009, S342-S346.
[13] H. Marijana, S. Kristina, K. Sandra, et al., Eur. J. Med. Chem. 46, 2011, 2274-2279.
[14] [K.C. Rout, R.R. Mohanty, S. Jena, K.C. Dash, Polyhedron 15, 1996, 1023.
[15] H. Chang, M. Fu, X.J. Zhao, E.C. Yang, J. Coord. Chem. 63, 2010, 3551.
[16] F.M. Nie, J. Chen, Z. Li, F. Lu, J. Coord. Chem. 63, 2010, 1711.
[17] M.Y. Duan, J. Li, Y. Xi, X.F. Lu, J.Z. Liu, G. Mele, F.X. Zhang, J. Coord. Chem. 63, 2010, 90.
[18] M. Akkurt, S. Karaca, H. Kucukbay, E. Orhan, O. Buyukgungor, Acta Cryst. 2005, E61, m41.
[19] H. Kucukbay, S. Gunal, E. Orhan, R. Durmaz. Asian J. Chem. 22, 2010, 7376.
[20] R.M. Mannar, K. Amit, E. Martin, R. Dieter, Inorg. Chem. 45, 2006, 5924-5937.
[21] Atta-ur-Rahman, M.I. Choudhary, W.J. Thomsen, Bioassay techniques for drug development, Harwood Academic Publishers, The Netherlands, 2001.
[22] K.S. Anil, M. Yasmin, R.A. Kamal, P. Om, Eur. J. Med. Chem. 38, 2003, 533-536.
[23] Atta-ur-Rahman, M.I. Choudhary, W.J. Thomsen, Bioassay techniques for drug development, Harwood Academic Publishers, The Netherlands, 2001.
[24] B. N. Meyer, N. R. Ferrigni, J. E. Putnam, et. al., Planta Med. 45, 1982, 31-34.
[25] A.W. Bauer, W.M. Kirby, J.C. Sherris, M. Turck, Am. J. Clin. Pathol. 45, 1966, 493-496.
[26] K. Nakamoto, Infrared and raman spectra of inorganic and coordination compounds, 5th edn. John Wiley & Sons Inc., New York, 1997.
[27] J.R. Ferrero, Low-frequency Vibrations of Inorganic and Coordination Compounds. Wiley-Interscience, New York, 1971.
[28] G. Singh, P.A. Singh, K. Singh, et. al., Proc. Nat. Acad. Sci. Ind. 72 A, 2002, 87-94.
[29] R. Sayaji, Asian J. Chem. 17, 2005, 2663-2668.
[30] W.W. Simons, The Sadtler handbook of proton NMR spectra, Sadtler Research Laboratories Inc. Philadelphia, 1978.
[31] D.J. Pasto, Organic structure determination, Prentice Hall International, London, 1969.
[32] S. Murugesan, S. Sathiyamoorthy, J. Pharm. Res. 4, 2011, 2679-2681.
[33] R. K. Agarwal, P. Garg, H. Agarwal, S. Chandra, Synth. React. Inorg. Met.-Org. Chem. 27, 1997, 251.
[34] P. K. Panchal, M. N. Patel, Synth. React. Inorg. Met.-Org. Chem. 34, 2004, 1277-1289.
[35] H. Koksal, M. Dolaz, M. Tilmer and S. Serin, Synth. React. Inorg. Met.-Org. Chem. 31, 2001, 1141-1162.
[36] G.G. Mohamed, Z.H. Abd El-Wahab. J. Therm. Anal. Calorim. 73, 2003, 347.
[37] Y.M. Essa, H.M. Abdel-Fattah, A.A. Soliman. J. Therm. Anal. 42, 1994, 1175.
[38] N.T. Abdel-Ghani, O. Esherif. Thermochim. Acta. 156, 1989, 69.
[39] M.A. Zayed, F.A. Nour El-Dien, G.G. Mohamed, N.E.A. El-Gamel. Spectrochim. Acta Part A, 60, 2004, 2843.
[40] Z.H. Chohan, C.T. Supuran, A. Scozzafava, J. Enzyme Inhib. Med. Chem. 19, 2004, 79-84.
[41] Z.H. Chohan, M. Praveen, Appl. Organomet. Chem. 15, 2001, 617-625.
Author Information
  • Institute of Chemical Sciences, Gomal University, D. I. Khan, KPK, Pakistan

  • Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan

  • Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan

  • Department of Chemistry, Govt. College, Gujranwala, Pakistan

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    Misbah ur Rehman, Muhammad Imran, Muhammad Arif, Muhammad Farooq. (2013). Metal-based Antimicrobial Agents: Synthesis, Characterization and Biological Studies of Mannich Base Derivatives of Benzimidazole and Their Metal Complexes. Science Journal of Chemistry, 1(5), 56-66. https://doi.org/10.11648/j.sjc.20130105.12

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    ACS Style

    Misbah ur Rehman; Muhammad Imran; Muhammad Arif; Muhammad Farooq. Metal-based Antimicrobial Agents: Synthesis, Characterization and Biological Studies of Mannich Base Derivatives of Benzimidazole and Their Metal Complexes. Sci. J. Chem. 2013, 1(5), 56-66. doi: 10.11648/j.sjc.20130105.12

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    AMA Style

    Misbah ur Rehman, Muhammad Imran, Muhammad Arif, Muhammad Farooq. Metal-based Antimicrobial Agents: Synthesis, Characterization and Biological Studies of Mannich Base Derivatives of Benzimidazole and Their Metal Complexes. Sci J Chem. 2013;1(5):56-66. doi: 10.11648/j.sjc.20130105.12

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  • @article{10.11648/j.sjc.20130105.12,
      author = {Misbah ur Rehman and Muhammad Imran and Muhammad Arif and Muhammad Farooq},
      title = {Metal-based Antimicrobial Agents: Synthesis, Characterization and Biological Studies of Mannich Base Derivatives of Benzimidazole and Their Metal Complexes},
      journal = {Science Journal of Chemistry},
      volume = {1},
      number = {5},
      pages = {56-66},
      doi = {10.11648/j.sjc.20130105.12},
      url = {https://doi.org/10.11648/j.sjc.20130105.12},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.sjc.20130105.12},
      abstract = {Novel Mannich base derivatives of Benzimidazole were prepared through the condensation reaction of benzimidazole derivative with formaldehyde and primary and/ secondary amine. Zinc(II), copper(II), nickel(II) and cobalt(II) complexes of Mannich bases have also been synthesized. All the compounds were fully characterized by, elemental analyses, magnetic moment determination, molar conductivity measurement, thermogravimetric analysis, spectral and analytical data. Experimental results showed that metal complexes act as bi-dentate ligands towards divalent metal ions via azomethine-N and deprotonated-O while suggesting an octahedral geometry. All the compounds were screened for in-vitro antibacterial and antifungal activity against various bacterial and fungal strains. Almost all the compounds showed good potent activity against microorganisms. It was also seen that compounds with complexed form were more active as compared to un-complexed form. The prepared compounds were also screened for their cytotoxicity and results showed that only Ni(II) complexes exhibit some cytotoxicity while all other compounds were almost inactive.},
     year = {2013}
    }
    

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  • TY  - JOUR
    T1  - Metal-based Antimicrobial Agents: Synthesis, Characterization and Biological Studies of Mannich Base Derivatives of Benzimidazole and Their Metal Complexes
    AU  - Misbah ur Rehman
    AU  - Muhammad Imran
    AU  - Muhammad Arif
    AU  - Muhammad Farooq
    Y1  - 2013/11/20
    PY  - 2013
    N1  - https://doi.org/10.11648/j.sjc.20130105.12
    DO  - 10.11648/j.sjc.20130105.12
    T2  - Science Journal of Chemistry
    JF  - Science Journal of Chemistry
    JO  - Science Journal of Chemistry
    SP  - 56
    EP  - 66
    PB  - Science Publishing Group
    SN  - 2330-099X
    UR  - https://doi.org/10.11648/j.sjc.20130105.12
    AB  - Novel Mannich base derivatives of Benzimidazole were prepared through the condensation reaction of benzimidazole derivative with formaldehyde and primary and/ secondary amine. Zinc(II), copper(II), nickel(II) and cobalt(II) complexes of Mannich bases have also been synthesized. All the compounds were fully characterized by, elemental analyses, magnetic moment determination, molar conductivity measurement, thermogravimetric analysis, spectral and analytical data. Experimental results showed that metal complexes act as bi-dentate ligands towards divalent metal ions via azomethine-N and deprotonated-O while suggesting an octahedral geometry. All the compounds were screened for in-vitro antibacterial and antifungal activity against various bacterial and fungal strains. Almost all the compounds showed good potent activity against microorganisms. It was also seen that compounds with complexed form were more active as compared to un-complexed form. The prepared compounds were also screened for their cytotoxicity and results showed that only Ni(II) complexes exhibit some cytotoxicity while all other compounds were almost inactive.
    VL  - 1
    IS  - 5
    ER  - 

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