Synthesis, single crystal XRD, DFT, molecular docking studies and antioxidant capacity and antibacterial evaluation of β -phenylethylamine derivative schiff base compound

Abstract

In this study, (E)-5-(((4-(dimethylamino)phenyl)imino)methyl)-2-methoxyphenol (K2) was synthesized and characterized. Its structure was determined by single crystal X-ray diffraction and was shown to belong to the monoclinic C2/c space group. By Hirshfeld surface analysis, the most dominant intermolecular interactions were found to be H···· H (%54,5), H···· C/C··· H (%25,2) and H···· O/O··· H (%12,4). The total surface area was calculated as 320.95 Ų. The geometry and reactivity of the molecule were investigated by DFT calculations (B3LYP/631G(d,p)). HOMO and LUMO energy values ​​were determined as -0.2820 eV and -0.11707 eV, respectively, and the energy gap was found as ΔEgap = 0.164 eV. Also, the polarizability was found as 399.94 a.u. and the dipole moment as 4.65 Debye. These theoretical calculations show that K2 can be easily polarized under an electric field and has a permanent dipole moment. Additionally, the antimicrobial and antioxidant properties of the compound were studied. It was found to be effective against Gram-positive and Gram-negative bacteria at a level comparable to Gentamicin and Ciprofloxacin. Furthermore, molecular docking simulations were performed to investigate the interaction of K2 with biologically important proteins (1NHJ, 3QX3, 2XO8 and 1HD2). K2 showed the strongest interaction with Human Peroxiredoxin 5 (1HD2) with a binding energy of -7.45 kcal/mol, suggesting that it may have antioxidant properties and may be a potential therapeutic candidate for oxidative stress-related diseases.