Design, Synthesis, and Anticancer of Some New Amide Derivatives from Coumarin-3-Carboxylic Acid Combined with Carbohydrate

Adam, Ruaa W.; Zimam, Ezzat H.

doi:10.21608/eajbsc.2023.308857

Design, Synthesis, and Anticancer of Some New Amide Derivatives from Coumarin-3-Carboxylic Acid Combined with Carbohydrate

Document Type : Original Article

Authors

Department of Chemistry, Faculty of Science, University of Kufa, Najaf, Iraq

10.21608/eajbsc.2023.308857

Abstract

A series of new coumarin derivatives based on carbohydrates were designed, and synthesized by employing the so-call ‘sugar-tail’ approach. The synthesis of amide derivatives involves the first step It includes the reduction of the azide sugar derivatives by hydrogen gas in the presence of activated palladium. The second step includes the reaction of the prepared amine derivatives with the carboxylic coumarin derivative to produce the amide derivatives. All of the compounds showed great water solubility and the pH value of their water solutions of compounds is 7.0. Docking simulation studies were performed to check the binding patterns of the synthesized compounds. The cytotoxicity potentials of 1,2,3-triazole glucosides derivatives were evaluated by MTT assay against liver cancer primary tissue culture after 48 hr., which appears that amide glucosides derivatives exhibited selective cytotoxicity against liver cancer cells isolated from Iraqi patients with inhibitory concentration (IC50) 106.81 μg/ml. Enzyme inhibition assay studies were also conducted for the epidermal growth factor receptor (EGFR), and the results explained the activity of a number of derivatives. All the synthesized compounds were characterized by IR, 1H, 13C NMR and Mass spectroscopy.

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