Novel Isoxazolone Based Azo Dyes: Synthesis, Characterization, Computational, Solvatochromic UV-Vis Absorption and Biological Studies

Abstract

• Novel isoxazolone based azo dyes were synthesised and spectroscopically characterized • Computational study- Frontier molecular orbitals, Mulliken population analysis, Global reactive parameters, Molecular electrostatic potential and Reduced density gradient analysis • Solvatochromic UV-Vis absorption study was carried out • Antimycobacterial and anti-inflammatory efficacy were studied In this research investigation, novel isoxazolone-thiazole based azo dyes ( Io1-Io4 ) were synthesized by a conventional azo coupling reaction at 0-5°C. The structure elucidation was precisely assessed using various spectroscopic techniques like FT-IR, NMR and HRMS. Through computational study, molecular geometry, mulliken atomic charges and global reactive descriptors were investigated to get a better insight into the molecular properties. Molecular electrostatic potential (MEP) and reduced density gradient analysis (RDG) were also examined. The solvatochromic UV-Vis absorption study was performed using different solvents. A diffuse reflectance study was carried out to determine the optical band gap of the synthesized novel dyes ( Io1-Io4) . Biological efficacy towards antimycobacterial and anti-inflammatory activity was examined and the results revealed that, the compounds showed very good antimycobacterial and anti-inflammatory activity.