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Synthesis, characterization, and evaluation of antioxidant and antibacterial activities of novel indole-hydrazono thiazolidinones

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Abstract

Three-component reactions of oxindole derivatives, thiosemicarbazide with dialkyl acetylenedicarboxylate (or maleimide) led to novel indole-hydrazono thiazolidinones in high-to-excellent yields. The antioxidant activities of the synthesized compounds were studied by 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. Among the products, those with amide moiety exhibited better antioxidant activities than other ester derivatives of indole-hydrazono thiazolidinones. Minimum bactericidal concentration (MBC) was evaluated against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) at different concentrations. However, the MBC values for compounds with amide group in their skeleton exhibited higher antibacterial activity than compounds with ester group. Therefore, it is assumed that these compounds could be used as effective antioxidant and antibacterial agents.

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Acknowledgements

We gratefully acknowledge financial support from the Research Council of University of Mazandaran.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, 47416-95447, Iran

    Sakineh Asghari & Maryam Pourshab

  2. Nano and Biotechnology Research Group, University of Mazandaran, Babolsar, 47416-95447, Iran

    Sakineh Asghari & Mojtaba Mohseni

  3. Department of Microbiology, Faculty of Science, University of Mazandaran, Babolsar, 47416-95447, Iran

    Mojtaba Mohseni

Authors
  1. Sakineh Asghari
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  2. Maryam Pourshab
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  3. Mojtaba Mohseni
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Correspondence to Sakineh Asghari.

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Asghari, S., Pourshab, M. & Mohseni, M. Synthesis, characterization, and evaluation of antioxidant and antibacterial activities of novel indole-hydrazono thiazolidinones. Monatsh Chem 149, 2327–2336 (2018). https://doi.org/10.1007/s00706-018-2292-x

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  • DOI: https://doi.org/10.1007/s00706-018-2292-x

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