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Synthesis, antidiabetic activity and molecular docking studies of novel aryl benzylidenethiazolidine-2,4-dione based 1,2,3-triazoles

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Abstract

A series of novel aryl benzylidenethiazolidine-2,4-dione based 1,2,3-triazoles synthesized in a straightforward route consisting of benzylidenethiazolidine-2,4-dione and 1,2,3-triazole pharmacophores. The new scaffolds tested for in vitro antidiabetic activity by inhibition of aldose reductase enzyme and its inhibition measured in half of Inhibition Concentration (IC50). The activity results correlated with standard reference Sorbinil (IC50: 3.45 ± 0.25 µM). Among all the titled compounds 8f (1.42 ± 0.21 µM), 8d (1.85 ± 0.39 µM), 13a (1.94 ± 0.27 µM) and 8b (1.98 ± 0.58 µM) shown potent activity. In addition, molecular docking results against the crystal structure of aldose reductase (PDB ID: 1PWM) revealed that the binding affinities shown by all synthesized compounds are higher than the reference compound Sorbinil. The docking scores, H-bond interactions, and hydrophobic interactions well defined inhibition strength of all compounds.

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Acknowledgements

The authors P. Nagesh and others expressed sincere thanks to UGC, 124257, New Delhi for Financial support. The authors thank the Head, Department of Chemistry, Osmania University, Hyderabad for providing lab facilities. CFRD Osmania University for analytical assistance. We thank DST PURSE for financial support.

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  1. Molecular Modelling and Medicinal Chemistry Laboratory, Department of Chemistry, Osmania University, Hyderabad, Telangana, 500007, India

    Nagesh Patnam, Kishan Chevula, Prasad Chennamsetti, Balaswamy Aleti & Vijjulatha Manga

  2. Telangana Mahila Viswavidyalayam, Hyderabad, Telangana, 500095, India

    Vijjulatha Manga

  3. Department of Sciences and Humanities, Matrusri Engineering College, Hyderabad, Telangana, 500059, India

    Aruna Kumari Kotha

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The authors NP, KC, PC and BA carried out all laboratory experiments, prepared the manuscript. KA performed docking studies. The entire work was carried out under the supervision of corresponding author VM.

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Patnam, N., Chevula, K., Chennamsetti, P. et al. Synthesis, antidiabetic activity and molecular docking studies of novel aryl benzylidenethiazolidine-2,4-dione based 1,2,3-triazoles. Mol Divers (2023). https://doi.org/10.1007/s11030-023-10674-y

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