Abstract
We herein report the facile synthesis of a series of 3,5-substituted-1,2,4-oxadiazole derivatives 9a–e and 10a–e in good to excellent yields by employing NMI-MsCl mediated amide bond formation reaction. The anti-inflammatory potential of the newly synthesized compounds were evaluated by anti-denaturation assay using diclofenac sodium as the reference drug. The compounds 9a and 9d demonstrated promising activity profile when compared to the reference standard. The SAR and molecular docking studies were also carried out for obtaining more details about the profound activity profile of the synthesized molecules. The synthesized compounds were docked against two target proteins TGF-β and IL-1 by AutoDock vina and Auto Dock 4.2.
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References
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Acknowledgements
The authors are thankful to Bharathiar University, Coimbatore, and Nagarjuna College of Engineering & Technology, Bengaluru, for providing all the facilities to carry out the research work. The authors are also thankful to Indian Institute of Science, Bengaluru, for providing the analytical data and spectra. Grigory V. Zyryanov is thankful to Ministry of Science and Higher Education of the Russian Federation (Grant # 075-15-2020-777) for the financial support. Sougata Santra is thankful to Russian Science Foundation (Grant # 20-73-10205) and Grants Council of the President of the Russian Federation (# NSh-1223.2022.1.3). Muthipeedika Nibin Joy is thankful to Russian Science Foundation (Grants ## 22-23-20189 and 21-13-00304). The detailed experimental procedure and characterization data including spectra are available in the Supporting Information uploaded along with the manuscript.
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BK and AMS conducted the synthesis and purification of the compounds. MNJ, SS and GVZ carried out the anti-inflammatory activity studies. PCN and MBA evaluated the docking studies. KS and MK wrote the manuscript and reviewed it.
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Kulkarni, B., Manjunatha, K., Joy, M.N. et al. Exploration of NMI-MsCl mediated amide bond formation for the synthesis of novel 3,5-substituted-1,2,4-oxadiazole derivatives: synthesis, evaluation of anti-inflammatory activity and molecular docking studies. Mol Divers 27, 1867–1878 (2023). https://doi.org/10.1007/s11030-022-10536-z
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DOI: https://doi.org/10.1007/s11030-022-10536-z