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

Suganya Murugan; Jayasudha Nehru; David Stephen Arputharaj; Anaglit Catherine Paul; Prasanth Gunasekaran; Necmi Dege; Emine Berrin Çinar; Kasthuri Balasubramani; Jose Kavitha Savaridasson; Abdullah G Al-Sehemi; Venkatachalam Rajakannan; Madhukar Hemamalini

doi:10.1016/j.heliyon.2022.e10070

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

Heliyon. 2022 Aug 5;8(8):e10070. doi: 10.1016/j.heliyon.2022.e10070. eCollection 2022 Aug.

Affiliations

¹ Department of Chemistry, Mother Teresa Women's University, Kodaikanal, India.
² Department of Physics, PSG College of Arts and Science, Coimbatore, India.
³ Centre of Advanced Study in Crystallography and Biophysics, University of Madras, Chennai, India.
⁴ Department of Physics, Ondoku Mayis University, Samsun, Turkey.
⁵ Department of Chemistry, Government Arts College (Autonomous), Karur, India.
⁶ Research Centre for Advanced Materials Science, King Khalid University, Abha 61413, Saudi Arabia.

Abstract

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.

Keywords: Anti-bacterial activity and MTT-assay; Crystal structure; DFT; Molecular docking; NCI index; Swiss ADME studies.