Synthesis and characterization of 2-(3,4-dihydroxyphenyl)-4-((4-hydroxyphenyl)imino)-4h-chromene-3,5,7-triol: In vitro biological evaluation and computational analysis

Abstract

Secondary phenolic metabolites like flavonoids, that are found in numerous plant sections and have a range of uses. Quercetin falls under the category of flavonols, belonging to the flavonoids found in various medicinal plants, some common fruits, and vegetables with various applications. However, quercetin, with its various applications, is not well established in the pharmaceutical industry since it is associated with a lot of drawbacks, like instability in the gastrointestinal tract, the first-pass effect, solubility issues, etc. Quercetin-Schiff base derivatives are essential for targeting cancer cells and enhancing biological activities due to the formation of the C=N (imine group), which plays a major role in enhancing biological activities. In this research article, quercetin Schiff base (Q1sb) was synthesised and analysed using spectroscopic techniques like ¹H NMR, ¹³C NMR, HRMS, etc. Biological activities like anti-bacterial, antioxidant, anti-inflammatory, and cytotoxicity analyses were done on four cancer cell lines, namely A549, HeLa, HepG2, and MCF-7, and molecular docking were done on some of the common targets. The first section explains the characteristics of flavonoid, the therapeutic action and drawbacks of quercetin, and the importance of Schiff base derivatives; the second section explains the synthesis method and characterization; and the third section explains the biological applications and molecular docking studies.