Design, Synthesis of Dioxopiperidinamide Derivatives by Amide Coupling Reaction and Study of Their Biological Activity

Abstract

A series of fifteen dioxopiperidinamide derivatives synthesized and their spectra chemical data were reported. An alternative amide coupling reaction has been followed by using 3-aminopiperidine-2,6-dione through amide bond functionalization between N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl) and Hydroxybenzotriazole (HOBt). All the designed compounds were docked in to the active sites of 2 A73: Human Complement Component C3. All the docked compounds is favorable to make both hydrogen and hydrophobic interaction with amino acids located at the binding site. The most of potential compounds (E)-N-(2,6-dioxopiperidin-3-yl)-3-(m-tolyl)acrylamide (4 g), (E)-3-(4-bromophenyl)-N-(2,6-dioxopiperidin-3-yl)acrylamide (4 h) and N-(2,6-dioxopiperidin-3-yl)-3-methyl-4-oxo-4,6,7,8,9,10-hexahydrothieno [2′,3′:4,5]pyrimido[1,2-a]azepine-2-carboxamide (7) studied for their anticancer activity on the THP-1 cancer cells line. It was also further established their Anti-inflammatory activity and Antioxidant activity with the comparable efficiency against those of clinically used drugs.