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New thiazolidine-2,4-diones as antimicrobial and cytotoxic agent

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Abstract

New (Z)-5-substituted-2,4-thiazolidinediones (3a–m) were easily prepared by the condensation of thiazolidine-2,4-dione (1) with suitable aldehydes (2a–m) via microwave irradiation technique. The reaction between (Z)-5-substituted-2,4-thiazolidinediones and 4-(bromomethyl) benzoic acid, using potassium carbonate as base in refluxing acetone, followed by a workup in acidic medium provided 4-(((Z)-5-substituted-2,4-dioxothiazolidin-3-yl)methyl) benzoic acid derivatives (4a–m). The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR spectral studies, and elemental analysis. All compounds were evaluated for their in vitro antimicrobial and cytotoxic activities. Antibacterial and antifungal results revealed that most of the compounds showed significant activity where as compounds 4c and 4g are found to be broad spectrum antibacterial and antifungal properties, the MIC values were observed in the range of 2–4 and 2–8 μg/ml, respectively. In MTT cytotoxicity studies, the compound 4g was found most potent. In HeLa, HT29, A549, and MCF-7 cells, the IC50 values were observed in the range of 30–36 μM.

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Acknowledgments

Authors are grateful to Dr. A. D. Taranalli, Principal, for providing necessary facilities. Authors are also grateful to NMR Research center, IISC, Bangalore, India, for providing the spectral data.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, KLE University’s College of Pharmacy, Belgaum, Karnataka, 590 010, India

    Shankar G. Alegaon & Kallanagouda R. Alagawadi

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  1. Shankar G. Alegaon
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  2. Kallanagouda R. Alagawadi
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Correspondence to Shankar G. Alegaon.

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Alegaon, S.G., Alagawadi, K.R. New thiazolidine-2,4-diones as antimicrobial and cytotoxic agent. Med Chem Res 21, 3214–3223 (2012). https://doi.org/10.1007/s00044-011-9876-x

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