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Synthesis and characterization of derivatives including thiazolidine-2,4-dione/1-H- imidazole and evaluation of antimicrobial, antioxidant, and cytotoxic properties of new synthetic heterocyclic compounds

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Abstract

Several new derivatives of thiazolidine-2,4-dione and 1-H-imidazole were prepared using imidazole aldehydes 6a–6f in ethanol as a solvent. Products 7a–7f were obtained in reasonable yields and great purity. The antioxidant activity for finish products was evaluated by DPPH radical scavenging activity and showed relatively good activity against ascorbic acid. Compounds 7d, 7e, and 7f had the highest antioxidant activity. Compound 7c showed the lowest amount of IC50 versus ascorbic acid. The antimicrobial activity of these compounds against gram-positive bacteria including Bacillus anthracis (B. anthracis) and Staphylococcus aureus (S. aureus) and gram-negative bacteria including Escherichia coli (E. coli) and Pseudomonas aeruginosa (P. aeruginosa) bacteria was evaluated by the inhibition zone diameter assay method, and the compounds showed moderate to low antibacterial activity. The toxicity properties of all synthesized compounds against cisplatin were investigated. Most of the compounds showed good activity against the positive control group, and the toxicity of compound 7b was higher than that of other compounds.

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Acknowledgements

This probe was supported in part by the Research Committee of the University of Guilan. We also thanks Dr. M. Pasandideh Nadamani for his useful synthetic advising and Dr. Esmaeel Panahi Kokor for the Cytotoxic MTT assay

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  1. Department of Organic Chemistry, Faculty of Science, University of Guilan, Rasht, Iran

    Hadiseh Yazdani Nyaki & Nosrat O. Mahmoodi

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  1. Hadiseh Yazdani Nyaki
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  2. Nosrat O. Mahmoodi
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Correspondence to Nosrat O. Mahmoodi.

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Nyaki, H.Y., Mahmoodi, N.O. Synthesis and characterization of derivatives including thiazolidine-2,4-dione/1-H- imidazole and evaluation of antimicrobial, antioxidant, and cytotoxic properties of new synthetic heterocyclic compounds. Res Chem Intermed 47, 4129–4155 (2021). https://doi.org/10.1007/s11164-021-04525-4

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