Biological evaluation of 2-(3,4-dihydroxyphenyl)-4-((4-methoxyphenyl)imino)-4H-chromene-3,5,7-triol: Design, synthesis, and molecular docking studies

Abstract

Plant materials are known to contain a category of naturally occurring compounds referred to as flavonoids. Quercetin is classified as a flavonol, which is present in various parts of plants and serves multiple functions within biological systems. This article outlines the synthesis of quercetin Schiff base (Qpa) through a condensation reaction involving quercetin and p-anisidine, followed by characterization using spectroscopic methods such as FTIR, UPLC, ¹H NMR, ¹³C NMR, elemental analysis, and HRMS. The biological applications of Qpa were investigated through antioxidant assays, anti-inflammatory tests, antibacterial evaluations, cytotoxicity assessments, and molecular docking studies. The results indicated that the ¹H NMR and ¹³C NMR spectra exhibited a distinct peak for OCH₃ at 3.66 and 55.73 ppm, respectively. In terms of biological activity, Qpa demonstrated significant antioxidant and anti-inflammatory effects at concentrations of 142.7 μg/mL ± 0.0015 and 247 μg/mL ± 0.0015, respectively. Additionally, Qpa exhibited antibacterial properties comparable to the positive control against both gram-positive and gram-negative bacteria at a concentration of 248 μg. Cytotoxicity studies revealed that Qpa had pronounced effects on MCF-7 and HepG2 cell lines. Furthermore, molecular docking analyses indicated that Qpa displayed high binding energy with AKT, tRNA synthetase, and TNF-α. Future in vivo studies are recommended to elucidate the specific mechanisms of action and to achieve significant results in the pursuit of a novel therapeutic agent.