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Synthesis of New Drug-Like Piperazine-2,5-diones by the Ugi/Tandem Process Catalyzed by TMSOTf and Their Molecular Docking

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Abstract

A new four-components post-Ugi transformation process has been studied. It provides an efficient access to biologically active piperazine-2,5-dione derivatives in high yield. The framework of piperazine-2,5-dione derivatives has been constructed by a tandem-decarboxylation of α-keto carboxylic acids promoted by a green catalyst trimethylsilyl trifluoromethane sulfonate (TMSOTf). Molecular docking study of piperazine-2,5-dione derivatives has been performed with various anticancer target proteins: human androgen receptor (AR) (PDB ID: 1E3G), human steroidogenic cytochrome P450 17A1 (PDB ID: 4NKV), epidermal growth factor receptor 2 HER2 (PDB ID: 3PP0), and estrogen receptor alpha (ERα) (PDB ID: 1A52), and has indicated their possible efficient interactions via hydrogen bonds.

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ACKNOWLEDGMENTS

Authors gratefully thank Leicester University, UK for performing 1H, 13C NMR, FTIR, HRMS spectra, and HPLC analysis.

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This work was financially supported by the authors.

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Authors and Affiliations

  1. Department of Chemistry, College of Education for Pure Sciences, Basrah University, 61004, Basrah, Iraq

    A. M. Jassem, A. M. Dhumad & F. A. K. Almashal

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  1. A. M. Jassem
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  2. A. M. Dhumad
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  3. F. A. K. Almashal
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Correspondence to A. M. Jassem.

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Jassem, A.M., Dhumad, A.M. & Almashal, F.A.K. Synthesis of New Drug-Like Piperazine-2,5-diones by the Ugi/Tandem Process Catalyzed by TMSOTf and Their Molecular Docking. Russ J Gen Chem 90, 2181–2188 (2020). https://doi.org/10.1134/S1070363220110262

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