Β-CYCLODEXTRIN ENCAPSULATION OF (E)-7-(DIETHYLAMINO)-3-((3-HYDROXYNAPHTHALEN-2-YL)IMINOMETHYL)-2H-CHROMEN-2-ONE SCHIFF BASE: SYNTHESIS, SPECTROSCOPIC CHARACTERIZATION AND POTENT ANTIMICROBIAL PROPERTIES

Abstract

Coumarin-based Schiff bases have received much interest in medicinal and supramolecular chemistry due to their diverse nature, easy synthetic accessibility, and wide-ranging bioactivity. This article describes the synthesis, characterization, and preparation of the β-cyclodextrin inclusion complex of a new Schiff base based on coumarin structure, (E)-7-(diethylamino)-3-(((3-hydroxynaphthalen-2-yl)imino)methyl)-2H-chromen-2-one. Characterization of the Schiff base compound and its inclusion complex was performed by Fourier Transform Infrared Spectroscopy, Carbon-13 Nuclear Magnetic Resonance, and Mass Spectrometry. It can be clearly seen that inclusion complex showed better results in terms of solubility and bioavailability compared to Schiff base alone. In vitro testing of its antimicrobial efficacy showed higher inhibition of selected bacteria and fungi due to the improved dissolution properties of the compound along with increased cellular uptake after encapsulation in the inclusion complex. Thus, it is evident that β-cyclodextrin encapsulation can serve as an effective approach towards increasing pharmacological activity of coumarin-based Schiff bases as antimicrobial agents.