MEDICINAL CHEMISTRY RESEARCH, vol.00, no.00, pp.1-11, 2023 (SCI-Expanded)
In this study, a total of 13 compounds (5–17) were synthesized starting from oleanolic acid (OA), a natural triterpenoid. Five new compounds (10, 11, 12, 15 and 17),
are the main targets of the study, which were synthesized for the first
time in this work as oxime, imine and hydrazone derivatives of OA.
Other compounds were previously obtained as natural or
semi-synthetically. NMR and HRMS analyses were carried out to determine
of structures of all the synthesized molecules. The inhibitory effects
of the synthesized compounds on acetylcholinesterase (AChE), human
carbonic anhydrase I (hCA I) and II (hCA II) were evaluated. Compounds 13 and 15
showed better inhibitory activity than the other compounds against both
hCA I and hCA II isoenzymes, which are competing with AZA. In addition,
compound 15 showed the strongest AChE inhibitory activity among all the tested compounds, with an IC50 value of 34.46 µM.