Synthesis of 3-Methoxy-6- [(2, 4, 6-trimethyl-phenylamino)-methyl]-phenol Schiff base characterized by spectral, in-silco and in-vitro studies

Murugan S., Nehru J., Arputharaj D. S., Catherine Paul A., Gunasekaran P., DEGE N., ...More

Heliyon, vol.8, no.8, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 8 Issue: 8
  • Publication Date: 2022
  • Doi Number: 10.1016/j.heliyon.2022.e10070
  • Journal Name: Heliyon
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, CAB Abstracts, Food Science & Technology Abstracts, Veterinary Science Database, Directory of Open Access Journals
  • Keywords: Anti-bacterial activity and MTT-assay, Crystal structure, DFT, Molecular docking, NCI index, Swiss ADME studies
  • Ondokuz Mayıs University Affiliated: Yes


The structure of the title compound (I) (C17H19NO2)2 the Schiff base, {3-Methoxy-6-[(2,4,6-trimethyl-phenylamino)-methyl]-phenol} was characterized by 1H, 13C NMR, UV–VIS and IR spectroscopic techniques. The crystal structure was determined by X-ray analysis. The compound (I) was crystallized in the Monoclinic space group P21/c, with a = 25.9845 (12), b = 7.3318 (4), c = 16.3543 (8) Å, β = 100.713(°) (4), and Z = 8. The intermolecular interactions of the compound (I) was analyzed using Hirshfeld surface and Fingerprint analysis. Based on the crystal-void calculation, the volume of the void and surface area of the Schiff base compound (I) was described. The frontier molecular orbital energy gap reveals charge transfer interactions involving donors and acceptors. The invitro studies on antibacterial property of the title compound shows best MIC value for Staphylococcus aureus and the compound effect on MTT assay on A549 lung cancer cell line. The molecular docking result shows that the compound has good molecular-level interaction with anticancer drug target having good interactions with active site residues. The non-covalent interactions in the protein-ligand complex were well established from NCI analysis.