Synthesis, spectroscopic characterization, crystal structure, interaction with DNA, CTAB as well as evaluation of biological potency, docking and Molecular Dynamics studies of N-(3,4,5-trimethoxybenzylidene)-2, 3-dimethylbenzenamine

Abstract

A novel N-substituted Schiff base ligand: N-(3,4,5-trimethoxybenzylidene)-2,3-dimethylbenzenamine was designed and successfully characterized by several spectroscopic techniques. The formation of the desired compound was confirmed by the appearance of CN peak at 1691 cm−1 in FT-IR spectrum. Similarly, in 1H and 13C NMR spectra, the peaks at 8.22 ppm for azomethine proton (HCN) and 158.8 ppm for azomethine carbon (CN) confirm the formation of the synthesized compound. DNA interaction of the compound was screened by using UV–visible spectroscopy and viscometry measurements confirming an intercalation mode. The interaction of compound with CTAB (Cetyl trimethylammonium bromide) was also studied by conductometric method showing a strong interaction with CTAB. The IC50 value of the current compound was highly efficacious upon comparison with the standard Glucantime used. This activity represents a higher multitude interaction, which might be a cause of enhanced antileishmanial activity. Cytotoxicity results showed that this compound is highly active even at lower concentrations and is biocompatible, making it a promising drug candidate for further investigations in this field. The experimental data were auxiliary supported by molecular docking studies in order to explore their binding behavior and the stability of the molecule due to its interaction within the receptor active site.