An efficient synthesis of 2,3-diaryl-2-azabicyclo[2.2.2]octan-5-ones and their acetylcholinesterase inhibitory activity

A series of substituted 2,3-diaryl-2-azabicyclo[2.2.2]octan-5-ones have been prepared by an efficient three-component aza-Diels–Alder cycloaddition reaction in water catalyzed by layered α-zirconium hydrogen phosphate (α-ZrP) and sodium calix[4]arene sulfonates bearing pendant short aliphatic chains. The 18 synthesized compounds were assayed for acetylcholinesterase inhibition using mouse acetylcholinesterase.

Graphical abstractA series of substituted 2,3-diaryl-2-azabicyclo[2.2.2]octan-5-ones have been prepared by an efficient three-component aza-Diels–Alder cycloaddition reaction in water catalyzed by layered α-zirconium hydrogen phosphate (α-ZrP) and sodium calix[4]arene sulfonates bearing pendant short aliphatic chains. The 18 synthesized compounds were assayed for acetylcholinesterase inhibition using mouse acetylcholinesterase.Figure optionsDownload full-size imageDownload as PowerPoint slide