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Design, synthesis and evaluation of novel thiazolidinedione derivatives as anti-hyperglycemic and anti-hyperlipidemic agents

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Abstract

A novel series of thiazolidine-2,4-diones was designed, synthesized and investigated for anti-diabetic activity. The (2,4-dioxo-1,3-thiazolidin-5-yl)methylphenylbenzamide derivatives contain an amide linkage between the central aryl ring and the hydrophobic tail. Structures of the compounds were confirmed by spectroscopic techniques fourier transform infrared spectroscopy, 1H-nuclear magnetic resonance and elemental (C, H, N) analysis. The synthesized compounds were evaluated for their in-vivo pharmacological activity (blood glucose and triglyceride lowering activity), where compounds thiazolidinediones-C and thiazolidinediones-E showed significant effects, comparable to the standard pioglitazone. Computational studies positively substantiated the nature and interaction of the designed compounds with peroxisome proliferator-activated receptor gamma.

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Acknowledgments

We would like to thank Indian Institute of Technology (BHU) for providing financial assistance through Sprouting grant for faculty (SGF) and Institute research project (IRP) scheme.

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Authors and Affiliations

  1. Pharmaceutical Chemistry Research Laboratory, Department of Pharmaceutics, Indian Institute of Technology (BHU), Varanasi, 221 005, India

    Sushant K. Shrivastava, Ankit Batham, Tanmaya K. Parida, Debapriya Garabadu & Priyanka K. Choubey

  2. Department of Pharmaceutical Sciences, Mohanlal Sukhadia University, Udaipur, 313001, India

    Saurabh K Sinha

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  1. Sushant K. Shrivastava
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  2. Ankit Batham
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  3. Saurabh K Sinha
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  4. Tanmaya K. Parida
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  5. Debapriya Garabadu
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  6. Priyanka K. Choubey
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Correspondence to Sushant K. Shrivastava.

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Shrivastava, S.K., Batham, A., Sinha, S.K. et al. Design, synthesis and evaluation of novel thiazolidinedione derivatives as anti-hyperglycemic and anti-hyperlipidemic agents. Med Chem Res 25, 2258–2266 (2016). https://doi.org/10.1007/s00044-016-1675-y

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  • DOI: https://doi.org/10.1007/s00044-016-1675-y

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