Citation: N.C. Desai, N.R. Shihory, G.M. Kotadiya. Facile synthesis of benzimidazole bearing 2-pyridone derivatives as potential antimicrobial agents[J]. Chinese Chemical Letters, ;2014, 25(2): 305-307. shu

Facile synthesis of benzimidazole bearing 2-pyridone derivatives as potential antimicrobial agents

  • Corresponding author: N.C. Desai, 
  • Received Date: 29 July 2013
    Available Online: 4 November 2013

  • A series of benzimidazole bearing 2-pyridones 5a-k were synthesized and assessed in vitro for their activity as antimicrobial agents using the conventional broth dilution method. The results of the antimicrobial study revealed that compounds 5b, 5c, 5j and 5k exhibited substantial antibacterial activity while compound 5d emerged as amore potent antifungal agent compared to the standard drugs chloramphenicol and ketoconazole, respectively. It was observed that the presence of inductively electron withdrawing groups remarkably enhance the antibacterial activity of the newly synthesized compounds. Cytotoxicity studies suggested that none of the tested compounds exhibited any significant cytotoxic effects.
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    1. [1]

      [1] A.Y. Saiki, L.L. Shen, C.M. Chen, J. Baranowski, C.G. Lerner, DNA cleavage activities of Staphylococcus aureusgyrase and topoisomerase IV stimulated by quinolones and 2-pyridones, Antimicrob. Agents Chemother. 43 (1999) 1574-1577.

    2. [2]

      [2] G. Ozturk, D.D. Erol, T. Uzbay, M.D. Aytemir, Synthesis of 4(1H)-pyridinone derivatives and investigation of analgesic and anti-inflammatory activities, Farmaco 56 (2001) 251-256.

    3. [3]

      [3] P. Storck, A. Aubertin, D.S. Grierson, Tosylation/mesylation of 4-hydroxy-3-nitro- 2-pyridinones as an activation step in the construction of dihydro[3,4-b] benzo[f][1,4]thiazepin-1-one based anti-HIV agents, Tetrahedron Lett. 46 (2005) 2919-2922.

    4. [4]

      [4] M.T. Cocco, C. Congiu, V. Onnis, New bis(pyridyl)methane derivatives from 4- hydroxy-2-pyridones: synthesis and antitumoral activity, Eur. J. Med. Chem. 38 (2003) 37-47.

    5. [5]

      [5] Q. Li, L.A. Mitscher, L.L. Shen, The 2-pyridone antibacterial agents: bacterial topoisomerase inhibitors, Med. Res. Rev. 20 (2000) 231-293.

    6. [6]

      [6] Y. Kohara, K. Kubo, E. Imamiya, et al., Synthesis and angiotensin Ⅱ receptor antagonistic activities of benzimidazole derivatives bearing acidic heterocycles as novel tetrazolebioisostere, J. Med. Chem. 39 (1996) 5228-5235.

    7. [7]

      [7] W.W. Mederski, D. Dorsch, S. Anzali, et al., Halothiophenebenzimidazoles as P1 surrogates of inhibitors of blood coagulation factor Xa, Bioorg. Med. Chem. Lett. 14 (2004) 3763-3769.

    8. [8]

      [8] M. Mader, A. de Dios, C. Shih, et al., Imidazolylbenzimidazoles and imidazo[4,5- b]pyridines as potent p38a MAP kinase inhibitors with excellent in vivo antiinflammatory properties, Bioorg. Med. Chem. Lett. 18 (2008) 179-183.

    9. [9]

      [9] H.H. Jardosh, C.B. Sangani, M.P. Patel, et al., One step synthesis of pyrido[1,2- a]benzimidazole derivatives of aryloxypyrazole and their antimicrobial evaluation, Chin. Chem. Lett. 24 (2013) 123-126.

    10. [10]

      [10] A. Andreani, M. Granaiola, A. Leoni, et al., Synthesis and antitubercular activity of imidazo[2,1-b]thiazoles, Eur. J. Med. Chem. 36 (2001) 743-746.

    11. [11]

      [11] V.K. Vladimir, G.B. Alicia, Recent developments in the design and synthesis of hybrid molecules basedonaminoquinoline ring and their antiplasmodial evaluation, Eur. J. Med. Chem. 44 (2009) 3091-3113.

    12. [12]

      [12] H.X. Ding, K.K.C. Liu, S.M. Sakya, et al., Synthetic approaches to the 2011 new drugs, Bioorg. Med. Chem. 21 (2013) 2795-2825.

    13. [13]

      [13] N.C. Desai, K.M. Rajpara, V.V. Joshi, Synthesis of pyrazole encompassing 2-pyridone derivatives as antibacterial agents, Bioorg. Med. Chem. Lett. 23 (2013) 2714-2717.

    14. [14]

      [14] N.C. Desai, V.V. Joshi, K.M. Rajpara, H.V. Vaghani, H.M. Satodiya, Facile synthesis of novel fluorine containing pyrazole based thiazole derivatives and evaluation of antimicrobial activity, J. Fluorine Chem. 142 (2012) 67-78.

    15. [15]

      [15] H.B. Lad, R.R. Giri, D.I. Brahmbhatt, An efficient synthesis of some new 3-bipyridinyl substituted coumarins as potent antimicrobial agents, Chin. Chem. Lett. 24 (2013) 227-229.

    16. [16]

      [16] P.C. Hannan, Guidelines and recommendations for antimicrobial minimum inhibitory concentration (MIC) testing against veterinary mycoplasma species, Vet. Res. 31 (2000) 373-395.

    17. [17]

      [17] P. Skehan, R. Strong, D. Scudiero, et al., New colorimetric cytotoxic assay for anticancer-drug screening, J. Natl. Cancer Inst. 82 (1990) 1107-1112.

    18. [18]

      [18] C.K. Ryu, K.U. Choi, J. Shin, et al., Synthesis and antifungal activity of 6-arylamino- 4,7-dioxobenzothiazoles, Bioorg. Med. Chem. 11 (2003) 4003-4008.

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