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Thiazolidinedione–triazole conjugates: design, synthesis and probing of the α-amylase inhibitory potential

    Rahul Singh

    Department of Chemistry, Kurukshetra University, Kurukshetra, 136119, India

    ,
    Parvin Kumar

    *Author for correspondence:

    E-mail Address: parvinchem@kuk.ac.in

    Department of Chemistry, Kurukshetra University, Kurukshetra, 136119, India

    ,
    Jayant Sindhu

    Department of Chemistry, COBS&H, CCS Haryana Agricultural University, Hisar, 125004, India

    ,
    Meena Devi

    Department of Chemistry, Kurukshetra University, Kurukshetra, 136119, India

    ,
    Ashwani Kumar

    Department of Pharmaceutical Sciences, GJUS&T, Hisar, 125001, India

    ,
    Sohan Lal

    Department of Chemistry, Kurukshetra University, Kurukshetra, 136119, India

    ,
    Devender Singh

    Department of Chemistry, Maharshi Dayanand University, Rohtak, 124001, India

    &
    Harish Kumar

    Department of Chemistry, School of Basic Sciences, Central University Haryana, Mahendergarh, 123029, India

    Published Online:https://doi.org/10.4155/fmc-2023-0144

    Aim: The primary objective of this investigation was the synthesis, spectral interpretation and evaluation of the α-amylase inhibition of rationally designed thiazolidinedione–triazole conjugates (7a–7aa). Materials & methods: The designed compounds were synthesized by stirring a mixture of thiazolidine-2,4-dione, propargyl bromide, cinnamaldehyde and azide derivatives in polyethylene glycol-400. The α-amylase inhibitory activity of the synthesized conjugates was examined by integrating in vitro and in silico studies. Results: The investigated derivatives exhibited promising α-amylase inhibitory activity, with IC50 values ranging between 0.028 and 0.088 μmol ml-1. Various computational approaches were employed to get detailed information about the inhibition mechanism. Conclusion: The thiazolidinedione–triazole conjugate 7p, with IC50 = 0.028 μmol ml-1, was identified as the best hit for inhibiting α-amylase.

    Graphical abstract

    Papers of special note have been highlighted as: • of interest; •• of considerable interest

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