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Synthesis, antimicrobial activity, and QSAR studies of amide-ester linked 1,4-disubstituted 1,2,3-triazoles

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Abstract

Synthesis of some amide-ester linked 1,4-disubstituted 1,2,3-triazoles was carried out by employing copper(I)-catalyzed 1,3-dipolar cycloaddition of 2-azido-N-substituted acetamides and benzoic acid prop-2-ynyl esters. All the synthesized 28 1,4-disubstituted 1,2,3-triazoles are new. The synthesized triazoles were characterized by IR, 1H NMR, 13C NMR, HRMS and evaluated for their antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Candida albicans, and Aspergillus niger. Compounds displaying potent antimicrobial activity against each of these microorganisms were found. Quantitative structure activity relationship studies for the synthesized compounds were also carried out to check the effect of various substituents in parent compound on antimicrobial activity.

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Acknowledgments

Authors wish acknowledge University Grants Commission, New Delhi for financial assistance to support research work through Major Research Project sanctioned to Dr. C. P. Kaushik (CPK).

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Authors and Affiliations

  1. Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, Haryana, India

    C. P. Kaushik, Krishan Kumar & Ashima Pahwa

  2. Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak, Haryana, India

    Balasubramanian Narasimhan

  3. Centre for Research and Development, IPCA Lab Ltd., Kandivali, Mumbai, Maharashtra, India

    Dharmendra Singh

  4. Centre for Pharmaceutical Sciences and Natural Products, Central University of Punjab, Bathinda, India

    Pradeep Kumar

Authors
  1. C. P. Kaushik
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  2. Krishan Kumar
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  3. Balasubramanian Narasimhan
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  4. Dharmendra Singh
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  5. Pradeep Kumar
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  6. Ashima Pahwa
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Correspondence to C. P. Kaushik.

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Kaushik, C.P., Kumar, K., Narasimhan, B. et al. Synthesis, antimicrobial activity, and QSAR studies of amide-ester linked 1,4-disubstituted 1,2,3-triazoles. Monatsh Chem 148, 765–779 (2017). https://doi.org/10.1007/s00706-016-1766-y

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  • DOI: https://doi.org/10.1007/s00706-016-1766-y

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