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Design, Synthesis, and Computational Characterization of Interesting Schiff Base Scaffolds as Antibacterial, Antimycobacterial, and Antifungal Agents

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Abstract

A series of (E)-1-(3/4-{[(E)-(2-chloroquinolin-3-yl)methylidene]amino}phenyl)ethan-1-one oximes 3a–3j have been designed and synthesized by the condensation of 2-chloroquinoline-3-carbaldehydes and (E)-1-(3/4-aminophenyl)ethan-1-one oximes using glacial acetic acid as a catalyst. The structures of the newly synthesized compounds were characterized by 1H and 13C NMR, FT-IR, and mass spectra. All compounds 3a–3j were assessed for their drug likeness and ADMET properties using computational analysis. They showed optimal drug scores and negligible toxicities and satisfied Lipinskiʼs rule of five. Compounds 3f, 3h, and 3i exhibited significant antimicrobial activity against Gram-positive (S. aureus, B. subtilis) and Gram-negative bacteria (S. Typhi, P. aeruginosa) and fungi (A. niger, A. flavus), whereas compounds 3g–3j showed antimyco­bacterial activity against Mycobacterium tuberculosis H37Rv strain with MIC in the range of 1.6 to 100 µg/mL.

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ACKNOWLEDGMENTS

The authors are grateful to Davanagere University for encouraging research activities and also thankful to the NMR Instrument Centre, Mangalore University, Mangala­gangothri, Karnataka, for carrying out the spectral analysis.

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This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

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Authors and Affiliations

  1. Department of Studies in Chemistry, Davangere University, Shivagangotri, 577007, Davanagere, Karnataka, India

    H. Maruthesh & B. P. Nandeshwarappa

  2. Department of Pharmaceutical Chemistry, Bapuji Pharmacy College, 577004, Davangere, Karnataka, India

    M. S. Katagi

  3. Institute of Bioinformatics and Applied Biotechnology, 560100, Bengaluru, Karnataka, India

    J. Samuel

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  1. H. Maruthesh
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  2. M. S. Katagi
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Maruthesh, H., Katagi, M.S., Samuel, J. et al. Design, Synthesis, and Computational Characterization of Interesting Schiff Base Scaffolds as Antibacterial, Antimycobacterial, and Antifungal Agents. Russ J Org Chem 59, 1783–1796 (2023). https://doi.org/10.1134/S1070428023100147

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