Giessel_2019_Bioorg.Chem_90_103058

Cinnamic anhydrides have been shown to be more than reactive reagents, but they also act as inhibitors of the enzyme acetylcholinesterease (AChE). Thus, out of a set of 33 synthesised derivatives, several of them were mixed type inhibitors for AChE (from electric eel). Thus, (E)-3-(2,4-dimethoxyphenyl)acrylic anhydride (2c) showed Ki=8.30+/-0.94microM and Ki'=9.54+/-0.38microM, and for (E)-3-(3-chlorophenyl)acrylic anhydride (2u) Ki=8.23+/-0.93microM and Ki'=13.07+/-0.46microM were measured. While being not cytotoxic to many human cell lines, these compounds showed an unprecedented and noteworthy inhibitory effect for AChE but not for butyrylcholinesterase (BChE).