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Synthesis of novel Schiff base benzamides via ring opening of thienylidene azlactones for potential antimicrobial activities

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Abstract

3-Hydrazinyl-3-oxo-1-(thiophen-2-yl)prop-1-en-2-yl]benzamide (4) is identified as a key intermediate for the synthesis of some new 3-[aryl substituted hydrazinyl]-3-oxo-1-(thiophen-2-yl)prop-1-en-2-yl]benzamide (Schiff base compounds) (5a–5o). The nucleophilic attack of hydrazine hydrate on 2-phenyl-4-(thiophen-2-ylmethylidene)-1,3-oxazol-5(4H)-one (3) results in the breaking of heterocyclic 1,3-oxazol-5(4H)-one with the formation of compound (4). It contains a new bonding site for further nucleophilic attack of substituted aldehyde, resulting in the formation of an imine. Structures of newly synthesized compounds were established by IR, 1H NMR, 13C NMR, mass spectra and elemental analysis. Newly formed compounds were evaluated for their preliminary in vitro antibacterial and antifungal activity. From the activity studies, it was observed that, among all the derivatives, 5a, 5b, 5d, 5e 5f, 5g, and 5h showed potent antimicrobial activity. The time–kill study report of the most active compound 5e exhibited 100% growth inhibition of Candida albicans at 2 h and Pseudomonas aeroginosa at 4 h. From the in silico molecular docking studies, it was observed that compounds 5k and 5f best fit into the receptors, methionine tRNA synthase from Escherichia coli and glucosamine-6-phosphate enzymes from E. coli, respectively. The compound 5e also showed moderate binding capacity to the respective targets.

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Acknowledgements

SNK gratefully acknowledges the Manipal Institute of Technology, Manipal University, Manipal and SAIF Punjab university, Chandigarh for obtaining the NMR and Mass spectral data.

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Authors and Affiliations

  1. Department of Studies in Chemistry, Mangalore University, Mangalagangothri, Karnataka, 574 199, India

    Subbulakshmi Narasimha Karanth & Narayana Badiadka

  2. Department of Chemistry, Shree Madhwa Vadiraja Institute of Technology and Management (VTU Belgaum), Vishwothama Nagar, Bantakal, Udupi, Karnataka, 574115, India

    Subbulakshmi Narasimha Karanth

  3. Department of Industrial Chemistry, Mangalore University, Mangalagangothri, Karnataka, 574 199, India

    Sarojini Balladka Kunhanna

  4. Department of Genetics and Plant Breeding, College of Agriculture, University of Agricultural Sciences (Bangalore), Karekere, Hassan, Karnataka, 573 225, India

    Kenkere S. Shashidhara

  5. Department of Microbiology, Kasturba Medical College, Manipal University, Manipal, Karnataka, 576104, India

    Prakash Peralam Yegneswaran

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  1. Subbulakshmi Narasimha Karanth
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  2. Narayana Badiadka
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Correspondence to Narayana Badiadka.

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Karanth, S.N., Badiadka, N., Balladka Kunhanna, S. et al. Synthesis of novel Schiff base benzamides via ring opening of thienylidene azlactones for potential antimicrobial activities. Res Chem Intermed 44, 4179–4194 (2018). https://doi.org/10.1007/s11164-018-3362-8

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  • DOI: https://doi.org/10.1007/s11164-018-3362-8

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