Influence of structural modifications on the physicochemical and biological properties of 4-nitro aniline based azo derivatives

Abstract

This study examines the impact of structure on the physicochemical and biological properties of 4-nitroaniline-based formazyl and diazenyl compounds with non-identical substituents. The structures of the synthesized compounds were characterized by means of UV–visible, FTIR, NMR and mass spectral methods. The structures of the compounds were optimized at the CAM-B3LYP/6–31 + G(d,p) level. The HOMO‐LUMO energies, structure–activity relationships, and MEP surface analysis were investigated. Bathochromic shifts were observed for the investigated compounds with an increase in solvent polarity. In vitro studies against the bacterial strains S. aureus (15 mm, standard: 21) and E. coli (13 mm, standard: 20) revealed that the benzoyl derivative was more potent compared to others. In docking studies, the interaction between the compounds and the bacterial enzymes (PDB IDs 3VOB and 3MZF) and anti-cancer protein p53 (PDB ID 4MZI) showed that benzoyl derivatives exhibited the highest binding energies (kcal/mol) against 3VOB (−9.1), 3MZF (−8.3), and 4MZI (−7.6). This work is significant as it sheds light on the design of novel azo derivatives and explores their properties and applications.