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Synthesis, antimicrobial, and cytotoxic activities of novel benzimidazole derivatives bearing cyanopyridine and 4-thiazolidinone motifs

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Abstract

A series of 6-(1H-benzo[d]imidazol-2-yl)-2-(2-(3-nitrophenyl)-4-oxothiazolidin-yl)-4-(aryl)nicotinonitriles 5a–l were synthesized and characterized by IR, 1H NMR, 13C NMR, and mass spectrometry techniques. These novel compounds 5a–l were screened for their in vitro antimicrobial activity against different bacterial and fungal strains and in vitro cytotoxicity study (HeLa cell line) using MTT colorimetric assay. The results demonstrated that compounds 5c, 5e, and 5i–k exhibited excellent antibacterial activity, while compounds 5d, 5i, and 5k were found to be the most potent antifungal agents. From the standpoint of SAR studies, it was observed that the presence of electron donating groups remarkably enhanced the antimicrobial activity of newly synthesized compounds. Further, the results of preliminary MTT cytotoxicity studies on HeLa cells suggested that potent antimicrobial activity of 5c–e and 5i–k was accompanied by low cytotoxicity.

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Acknowledgments

Authors are thankful to the University Grants Commission, New Delhi and Department of Science & Technology, New Delhi for financial support under the NON-SAP and DST-FIST programs, respectively. One of the authors, G M Kotadiya is thankful to UGC, New Delhi for providing “Research Fellowships in Science to Meritorious Students.”

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Authors and Affiliations

  1. Division of Medicinal Chemistry, Department of Chemistry, UGC NON-SAP & DST-FIST Sponsored Department, Mahatma Gandhi Campus, Maharaja Krishnakumarsinhji Bhavnagar University, Bhavnagar, 364002, India

    N. C. Desai, D. D. Pandya, K. A. Bhatt, G. M. Kotadiya &  Priyanka Desai

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  1. N. C. Desai
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  2. D. D. Pandya
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  3. K. A. Bhatt
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  4. G. M. Kotadiya
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  5. Priyanka Desai
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Correspondence to N. C. Desai.

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Desai, N.C., Pandya, D.D., Bhatt, K.A. et al. Synthesis, antimicrobial, and cytotoxic activities of novel benzimidazole derivatives bearing cyanopyridine and 4-thiazolidinone motifs. Med Chem Res 23, 3823–3835 (2014). https://doi.org/10.1007/s00044-014-0971-7

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