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Synthesis, characterization and antimicrobial activity of 4-((1-benzyl/phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde analogues

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Abstract

A diverse series of 4-((1-benzyl/phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde analogues has been synthesized in good yield by the click reaction between 4-O-propargylated benzaldehyde and various organic bromides/azides. All the synthesized compounds were tested in vitro for their antimicrobial activity against Gram-positive bacteria (Staphylococcus epidermidis and Bacillus subtilis), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) and fungi (Candida albicans and Aspergillus niger). Most of the compounds exhibited good-to-excellent antimicrobial activity. Compound 7b was found to be more potent than ciprofloxacin against B. subtilis, whereas it showed activity comparable to ciprofloxacin against E. coli. Compounds 4h and 4i showed activity comparable to fluconazole against A. niger. Further, the binding mode of compound 7b into the active site of E. coli topoisomerase II DNA gyrase B has also been investigated.

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Acknowledgments

The authors are thankful to Dr. Anil Kumar, Department of Bio and Nanotechnology and Central Instrumentation Laboratory, Guru Jambheshwar University of Science and Technology, Hisar, India, for assisting in antimicrobial studies and providing NMR spectra of the compounds.

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Authors and Affiliations

  1. Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, 125001, India

    Kashmiri Lal & Pinki Yadav

  2. Department of Pharmaceutical Sciences, Guru Jambheshwar University of Science and Technology, Hisar, Haryana, 125001, India

    Ashwani Kumar

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  1. Kashmiri Lal
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  2. Pinki Yadav
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  3. Ashwani Kumar
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Correspondence to Kashmiri Lal.

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Lal, K., Yadav, P. & Kumar, A. Synthesis, characterization and antimicrobial activity of 4-((1-benzyl/phenyl-1H-1,2,3-triazol-4-yl)methoxy)benzaldehyde analogues. Med Chem Res 25, 644–652 (2016). https://doi.org/10.1007/s00044-016-1515-0

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  • DOI: https://doi.org/10.1007/s00044-016-1515-0

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