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Functionalized acridines, tetrahydroacridines and quinolines were evaluated for in vitro AChE and BChE inhibitory activities. Potent nanomolar inhibition of both enzymes was found in the tacrine-donepezil hybrid N-(1-benzylpiperidin- 4-yl)-6-chloro-1,2,3,4-tetrahydroacridin-9-amine (51). Molecular modelling and kinetic studies support the notion that 51 occupied the catalytic and peripheral anionic sites of AChE. The physicochemical properties (polar surface area, lipophilicity, hydrogen bonding characteristics) of 51 were within the threshold limits for permeability across the blood brain barrier. Thus, 51 is a promising hybrid inhibitor derived from two established AChE inhibitors with clinical relevance to neurodegenerative diseases.
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