Biological, electrochemical, molecular docking and DFT studies of the asymmetric Schiff base: synthesis of 2-hydroxy-6-methyl-3-((E)-1-((4-methyl-3-((E)- (pyridin-3-ylmethylene)amino)phenyl)imino)ethyl)-4H pyran-4-one

Abstract

The asymmetric Schiff base 2-hydroxy-6-methyl-3-((E)-1-((4-methyl-3-((E)-(pyridin-3-ylmethylene)amino)phenyl)imino)ethyl)-4H-pyran-4-one (AL) was synthesized, and characterized by LC-MS, FT-IR, UV-Vis, 1H and 13C NMR techniques as well as cyclic voltammetry. The optimized molecular structures, IR and UV-Vis spectral modeling, stability, reactivity, and specific quantum chemical properties of the synthesized AL were examined using Density Functional Theory (DFT). The theoretical findings were consistent with the experimental results. The results show that compound AL has good antioxidant and anti-inflammatory activity. The electrochemical behavior of AL and BHT in the presence of superoxide radicals shows that the radical reaction is spontaneous. Apro-AL calculations indicated the ability of the AL compound to inhibit the primary protease (4GCA). Finally, the docking studies and ADME-T results showed that the AL compound under investigation could be developed as a therapeutic agent.