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The derivatives of isoindoline-1,3-dione are interesting due to their biological activities, such as anti-inflammatory and antibacterial effects. Several series have been designed and evaluated for Alzheimer’s therapy candidates. They showed promising activity. In this work, six new derivatives were first tested in in silico studies for their inhibitory ability against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes. Molecular docking and molecular dynamic simulation were applied. Next, these compounds were synthesized and characterized by ¹H NMR, ¹³C NMR, FT-IR, and ESI–MS techniques. For all imides, the inhibitory activity against AChE and BuChE was tested using Ellaman’s method. IC₅₀ values were determined. The best results were obtained for the derivative I, with a phenyl substituent at position 4 of piperazine, IC₅₀ = 1.12 μM (AChE) and for the derivative III, with a diphenylmethyl moiety, with IC₅₀ = 21.24 μM (BuChE). The compounds tested in this work provide a solid basis for further structural modifications, leading to the effective design of potential inhibitors of both cholinesterases.