Tunc_2023_Chem.Biodivers__e202300207

Novel chiral benzimidazole amine hybrids (4a-4d) were synthesized from commercially available amine [R(+)-Phenylethylamine, S(-)-Phenylethylamine, R(-)-Cyclohexylethylamine, S(+)-Cyclohexylethylamine] and 2-(chloromethyl)-N-tosyl-1-H-benzimidazole. The synthesized compounds (4a-4d) were characterized by IR, NMR, and LC-MS analysis. The inhibitory effect of 4a-4d on human erythrocytes carbonic anhydrase I (hCAI), II (hCA-II), and acetylcholinesterase (AChE) activity was investigated. For hCA-I, the IC50 values of 4a-4d were found to be 4.895 microM, 1.750 microM, 0.173 microM, and 0.620 microM, respectively, and for hCA-II, the IC50 values of 4a-4d were found to be 0.469 microM, 0.380 microM, 0.233 microM, 0.635 microM, respectively. Furtheremore, IC50 values of 4a-4d on AChE were found as 87.5 nM, 100 nM, 26.92 nM, and 100 nM, respectively. In addition, molecular docking analysis was performed to evaluate the affinity of 4a-4d against hCA-I, hCA-II, and AChE and explain their binding interactions.