1,2,4-Triazol 4-Bromobenzenesulfonates: Synthesis, Characterization (IR, NMR), DFT, Enzym Activities, and Docking Study

Abstract

(E)-4-(((3-Methyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl) imino) methyl) phenyl 4-bromo benzene sulfonate (I) and (E)-4-(((3-benzyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl) imino) methyl) phenyl 4-bromo benzene sulfonate(II) were prepared and characterized by FTIR and NMR spectroscopic methods. Density functional theory (DFT) method with 6-311++G(d,p) basis set was used for the theoretical study of compounds I and II. Optimized molecular structures and spectral parameters were obtained for compounds. Theoretical spectral data were compared with experimental ones and the presence of intermolecular hydrogen bonds was evaluated. Results show that in the molecular structure of compounds are available N-H center dot center dot center dot O type strong intermolucular hydrogen bonds. In this study, the inhibition effects of compounds I, II on AChE and GST enzymes were investigated. While AChE enzyme inhibitors are used in the treatment of Alzheimer's disease, GST enzyme inhibitors can be used as anti-cancer drugs. Tacrine and ethacrynic acid were studied that widely used in the international arena, as standard inhibitors. As a result, we can say that the molecules we used in the study for the gst enzyme are good inhibitors. In silico analysis was performed to investigate the possible interactions between the synthesized compounds I, II and the receptor protein.