Theoretical and experimental approaches of new Schiff bases: efficient synthesis, X-ray structures, DFT, molecular modeling and ADMET studies

DEGE N., Raza M. A., Doğan O. E., Agar T., Mumtaz M. W.

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, vol.18, no.9, pp.2345-2368, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 18 Issue: 9
  • Publication Date: 2021
  • Doi Number: 10.1007/s13738-021-02194-z
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier
  • Page Numbers: pp.2345-2368
  • Keywords: Crystal structure, Density functional theory, Molecular modeling, Schiff base, ADMET
  • Ondokuz Mayıs University Affiliated: Yes


Two new Schiff bases (E)-1-(3-((2-hydroxy-3-methylbenzylidene)amino)phenyl)ethan-1-one (1) and (E)-2-(((3-chloro-4-(4-chlorophenoxy)phenyl)imino)methyl)-6-methylphenol (2) were synthesized by already reported method on reflux. Characterization of targeted compounds was performed by spectroscopic techniques and X-ray diffraction analysis. Single-crystal X-ray diffraction studies showed that compound 1 is orthorhombic, while 2 is triclinic. In the crystalline molecules, intermolecular interactions have been observed by using the Hirshfeld surface analysis along 2D interactions. Molecular Operating Environment software was used for the docking studies which administer the potential appliance of the targeted compounds against AChE and BChE. Results of the docking study depicted that compound 1 is less active than that of compound 2 across both enzymes. To perform the optimization of the Schiff base, 6-31G(d,p) basis set and B3LYP method were used. DFT calculations were used to measure the associated energies of the orbitals and also correlate the bond angle and bong length of the synthesized compounds with the experimental values. It was seen from results that experimental and DFT calculation are in close agreement. In order to check the therapeutic properties, in silico ADMET model was adopted which revealed that the different properties of the synthesized molecules are drug-like.