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Two- and three-directional synthesis by 3–7CRs of novel (imidazolidine/thiazolidine)-2,4-diones: preparation, antibacterial, anticonvulsant, and molecular docking investigation

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Abstract

A variety of new compounds containing two or three biologically active imidazolidine-2,4-dione and thiazolidine-2,4-dione (TZD) cores through two- and three-way optimization of 3 and 4CR by Knoevenagel condensation were synthesized (Method A). In another attempt, two and three Bucherer–Berg modified with 5 and 7CR directed to synthesize larger homologous molecules were used (Method B). The structure of these derivatives was confirmed by FT-IR, 1HNMR, 13CNMR, and Elemental analysis. To evaluate the anticonvulsant activity of these derivatives, all the compounds were considered to be studied through molecular docking for Anticonvulsant Drug Binding (ADB) to the Voltage-Gated Sodium Channel Inner Pore (VGCIP). The in-silico molecular docking study results showed that molecules 5c, 7, 9, and 10 among the synthesized compounds with − 8.31, − 9.23, − 8.91, and − 10.79 kJ mol−1 glide scores respectively, lead to more binding affinity toward the channel and fitting well in the active pocket, thus, they may be considered as good anticonvulsant agents. Also, to evaluate the antibacterial properties of these derivatives, the ligand–protein molecular docking calculation using the active sites of the following bacterial proteins has been performed. Gram-positive bacteria such as B. anthracis (PDB ID: 3TYE) and S. aureus (PDB ID: 3ACX) and gram-negative bacteria E. coli (PDB ID: 1AB4) and P. aeruginosa (PDB ID: 5U39). The most significant overall score has been obtained for S. aureus (PDB ID: 3ACX) bacteria. According to the calculation compound 10 leads to the most efficient antibacterial activity against two Gram-positive bacteria and compounds 4a and 7 with Gram-negative proteins bacterial. The highest binding affinity is related to compound 7 for the Gram-negative P. aeruginosa (PDB ID: 5U39) protein target. The antibacterial properties of these derivatives were also experimentally investigated confirming the results obtained by the ligand–protein molecular docking calculation.

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Acknowledgements

This probe was supported in part by the Research Committee of the University of Guilan.

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The Research Committee of the University of Guilan.

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Authors and Affiliations

  1. Department of Organic Chemistry and Pharmaceutical Chemistry, Faculty of Science, University of Guilan, Rasht, Iran

    Hadiseh Yazdani Nyaki & Nosrat O. Mahmoodi

  2. Department of Chemistry, Payame Noor University, Tehran, Iran

    Hossein Taherpour Nahzomi

  3. Medicinal Plants Research Center, Yasuj University of Medical Sciences, Yasuj, Iran

    Esmaeel Panahi Kokhdan

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  1. Hadiseh Yazdani Nyaki
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Contributions

NOM, supervised the findings of this work, conceived the presented idea, and edited it. HYN, conceived the presented idea, developed the theory, synthesized all compounds and prepared and revised figures and Tables, and fit them into the Manuscript. HTN, performed the computations of a Molecular Docking Study for Antibacterial Effect and Molecular docking studies for Anticonvulsant Drug Binding (ADB) to the Voltage-Gated Sodium Channel Inner Pore (VGCIP) (docking protein with synthesized compounds). EPK, performed the Antibacterial test and verified the analytical methods.All authors discussed the results and contributed to the final manuscript.

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Correspondence to Nosrat O. Mahmoodi.

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Yazdani Nyaki, H., Mahmoodi, N.O., Taherpour Nahzomi, H. et al. Two- and three-directional synthesis by 3–7CRs of novel (imidazolidine/thiazolidine)-2,4-diones: preparation, antibacterial, anticonvulsant, and molecular docking investigation. Res Chem Intermed 49, 4149–4175 (2023). https://doi.org/10.1007/s11164-023-05058-8

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