N-Benzyl Benzamide Derivatives as Selective Sub-Nanomolar Butyrylcholinesterase Inhibitors for Possible Treatment in Advanced Alzheimer’s Disease

Journal of Medicinal Chemistry
2022.0

Abstract

Herein, we report a series of selective sub-nanomolar inhibitors against butyrylcholinesterase (BChE). These compounds, bearing a novel <i>N</i>-benzyl benzamide scaffold, inhibited BChE with IC<sub>50</sub> from picomolar to nanomolar. The inhibitory activity was confirmed by the surface plasmon resonance assay, showing a sub-nanomolar <i>K</i><sub>D</sub> value, which revealed that the compounds exert the inhibitory effect through directly binding to BChE. Several compounds showed neuroprotective effects verified by the oxidative damage model. Furthermore, the safety of <b>S11-1014</b> and <b>S11-1033</b> was demonstrated by the in vivo acute toxicity test. In the behavior study, 0.5 mg/kg <b>S11-1014</b> or <b>S11-1033</b> exhibited a marked therapeutic effect, which was almost equal to the treatment with 1 mg/kg rivastigmine, against the cognitive impairment induced by Aβ<sub>1-42</sub>. The pharmacokinetics studies characterized the metabolic stability of <b>S11-1014</b>. Thus, <i>N</i>-benzyl benzamide inhibitors are promising compounds with drug-like properties for improving cognitive dysfunction, providing a potential strategy for the treatment of Alzheimer's disease.

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