Synthesis, characterization of a novel molecule containing imine group, investigation of its quantum chemical, molecular docking and ADME properties

Yilmaz Z. N. , DEDE B.

JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 2021 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2021
  • Doi Number: 10.1080/07391102.2021.1993339
  • Keywords: Schiff base, density functional theory, molecular docking, ADME, drug-likeness, SCHIFF-BASES, VIBRATIONAL ABSORPTION, ANTIMICROBIAL ACTIVITY, COMPLEXES, ANTIBACTERIAL, CYTOTOXICITY


In this study, a novel Schiff base, 2-[(4-dimethylamino-benzylidene)-amino]-3-(4-hydroxy-phenyl)-propionic acid (DMAT) was synthesized as a result of the condensation reaction of N,N-dimethylamino benzaldehyde and L-tyrosine. The structure of the molecule obtained was characterized by H-1- and C-13-NMR, FTIR, UV-Vis spectroscopy and elemental analysis. Density functional theory (DFT) was used to calculate the optimized geometry, vibrational wavenumbers and electronic parameters at the B3LYP level using 6-311 G(d,p) basis set. In addition, H-1- and C-13-NMR, FTIR and UV-Vis data of the DMAT molecule were calculated with the same DFT/B3LYP/6-311G(d,p) trinity and the spectra obtained from these calculations were compared to the experimental data. The interactions of the DMAT molecule with vascular endothelial growth factor receptor-2 (VEGFR-2) and beta-ketoacyl synthase (KAS III) proteins were investigated by molecular docking studies. The results obtained were then compared with the molecular docking results of the selected drug active substances Regorafenib and Isoniazid molecules. The best interaction was between DMAT-VEGFR-2 with -8.30 and -1586.97 kcal/mol binding energy and full fitness score, respectively. In addition, ADME properties of the DMAT molecule were examined and some drug-likeness, physicochemical, lipophilicity and pharmacokinetic properties of this molecule were determined. The ADME and Lipinski parameters of the DMAT molecule exhibited good drug-likeness properties.