Synthesis and anticholinesterase activity of new tacrine carbamate derivatives

In this study, 13 new tacrine derivatives (6a-k) containing carbamate groups were synthesized and their effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes were evaluated. Among the synthesized tacrine derivatives, ((1,2,3,4-tetrahydroacridin-9-yl)amino)ethyl(3-nitro phenyl) carbamate (6k) showed the best inhibitor activity against AChE and BuChE with IC50 value of 22.15 nM and 16.96 nM, respectively. In addition, in regard to structure-activity relationship, it can be seen that the inhibitory activity depends on the electronegativity, polarizability and binding position of the substituent on phenyl ring. Structures of the synthesized final products were verified by 1H NMR, 13C NMR, and IR spectrometers.