Synthesis and biological properties of new propanol amin derivates attached to 2-metoxifenol

In this study, the synthesis of seven new ß-amino alcohols was designed and performed by starting from eugenol, a natural phenolic compound known to be biologically active. The synthesized compounds (2a-f) were obtained in yields ranging from 54 to 81%. Molecule structures were determined with 1H NMR and 13C NMR spectroscopies. In addition, the inhibitory effects of these substances on acetylcholinesterase (AChE), alpha-glucosidase (α-Gly), human carbonic anhydrase I (hCAI) and human carbonic anhydrase II (hCAII) enzymes have been investigated. It has been seen that all compounds have a better ability to inhibit compared to existing tried inhibitors. Among these, the best inhibitor against AChE enzyme is 2b (Ki 62.08 ± 11.67 and IC50 90.33), and against α-Gly, 2c showed the highest effect (Ki 0.33 ± 0.08 and IC50 0.28). The best inhibitor against hCAI and hCAII enzymes is 2f compound. For hCAI and hCAII, Ki value was measured as 9.68 ± 1.32 and 11.46 ± 2.64 and IC50 values as 7.37 and 8.26, respectively. Keywords: eugenol, propanol amine, β-amino alcohols, epoxide, enzyme inhibition