Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones

This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3·Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure–activity relationship some trends are suggested.

Graphical abstractThis work describes the enantioselective synthesis and AChE Inhibitory activities of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Based on qualitative structure–activity relationship some trends are suggested.Figure optionsDownload full-size imageDownload as PowerPoint slide