7,8-Dihydroxycoumarin derivatives: In silico molecular docking and in vitro anticholinesterase activity

•A series of 7,8-dihydroxy coumarin derivatives was designed and synthesized.•All coumarins were tested in vitro anti-acetylcholinesterase and antioxidant activities.•Antioxidant mechanism and structure activity relationships of coumarins were discussed.•In silico molecular docking, DFT and ADMET properties of coumarins was evaluated.•The in silico results of coumarins were in agreement with the results of in vitro experiments. In this study, acetylcholinesterase enzyme (AChE) inhibition potential and antioxidant activity of eight different coumarin derivatives together with two (5 and 8) newly synthesized coumarins were investigated. The results showed that all compounds exhibited inhibitory activity on AChE. Compounds 1 (96.83%), 3 (96.72%), and 2 (95.48%) showed the highest inhibitory activity and the results were more significant than that of galantamine (93.14%). Compound 7 displayed the most potent inhibition of AChE (92.12%), close to galantamine. Molecular docking studies of AChE were carried out to support in vitro testing. In addition, the antioxidant activities of coumarins were performed with DPPH, FRAP, and CUPRAC methods. Among them, compound 7 had the highest results in all the assays. The pharmacokinetic properties of compounds were determined using ADMET estimates; target coumarins may be drug candidates for Alzheimer's disease, especially compound 7 may be used as an antioxidant agent in the future after detailed analysis.