(S)-Rivastigmine and twelve chiral analogues were synthesized starting from p-hydroxybenz- aldehyde or m-hydroxybenzaldehyde via (R)- or (S)-tert-butanesulfinylimines as a chiral initiator, and characterized by IR, ¹H NMR, ¹³C NMR and HR-MS techniques. Ellman’s method was applied to evaluate their bio-activities. Results showed that these compounds exhibited potent inhibitory activities of acetylcholinesterase and butyrylcholinesterase, some of them even superior to rivastigmine.

Key words: asymmetric synthesis, cholinesterase inhibitor, rivastigmine, analogue