Photophysical and antitubercular studies on newly synthesised structurally architectured sulphonamide

Abstract

This study presents the synthesis and characterisation of four mono-azo sulphonamide derivatives through diazo-coupling electrophilic substitution reactions. The structural analysis of the synthesised molecules was conducted utilising FT-IR, 1H-NMR and HR-MS techniques. Absorption and fluorescence maxima of the synthesised molecules were determined across solvents of varying polarity to explore Solvatochromic behaviour. Density functional theory was employed to elucidate electronic and optical properties, including the computation of HOMO–LUMO energies using Gaussian 09W software, with comparisons to experimental data. Molecular electrostatic potential 3D plots identified electrophilic and nucleophilic sites. Solvent interactions were evaluated using Kamlet–Abboud Taft and Catalan parameters. Further, global chemical reactivity descriptors were estimated to ascertain chemical reactivity of the molecules. Additionally, the effectiveness of the colourant anti-tubercular activity was evaluated using in vitro and molecular docking techniques. The biological activity results reveal that methyl-pyridone and barbituric acid coupled with sulphamethizole (SMP and SMB) displayed excellent anti-tubercular activity compared with the standard Gentamycin.