Design, synthesis and biological evaluation of novel 3,4-dihydro-2(1H)-quinoline-O-carbamate derivatives as AChE/MAO-B dual inhibitors for the treatment of Alzheimer's disease

设计、合成和生物学评价新型3,4-二氢-2(1H)-喹啉-O-氨基甲酸酯衍生物作为AChE/MAO-B双重抑制剂用于治疗阿尔茨海默病

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Abstract

Alzheimer's disease (AD) is an irreversible degenerative disorder of the brain, and there is no effective drug for it to date. Given its complex pathogenesis, the multi-target-directed ligand (MTDL) strategy is considered as a promising approach against AD. Herein, a series of 3,4-dihydro-2(1H)-quinoline-O-carbamate derivatives were designed and synthesized based on the MTDL strategy. The in vitro biological results indicated that 3c was a potent AChE/MAO-B dual inhibitor with an IC(50) value of 0.81 μM and 0.17 μM, respectively. Molecular modeling and molecular dynamics (MD) simulations offered possible insights into the AChE/MAO-B inhibition of 3c. Moreover, 3c showed good stability and BBB permeability, as well as favorable neuroprotective effects. In vivo evaluation exhibited that 3c impressively improved the AlCl(3)-induced zebrafish AD model by elevating ACh, decreasing APP and inflammatory factors. Further, 3c effectively alleviated the scopolamine-induced cognitive impairment model. Therefore, 3c is a promising AChE/MAO-B dual inhibitor for treating AD.

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