8‐Quinolinol‐Based Azo Analogues: Synthesis, Characterization, Computational ADME‐Tox, Molecular Docking and Drug‐Likeness Analysis, and Assessment of Their Antibacterial and Antifungal Activities

A series of 8‐quinolinol‐based azo analogues was synthesized in satisfactory yields via a simple one‐step protocol using substituted anilines and 8‐quinolinol as starting materials. The structures were confirmed by 1 H and 1 3 C NMR, FT‐IR spectroscopy, and elemental analysis. The antimicrobial activities were evaluated in vitro against four bacterial strains ( Escherichia coli , Micrococcus luteus , Staphylococcus aureus , and Pseudomonas aeruginosa ) and two fungal strains ( Candida glabrata and Candida albicans ) using agar well diffusion and minimum inhibitory concentration (MIC) assays. Among the tested compounds, analogues 3, 7, and 8 exhibited remarkable antibacterial and antifungal activities, comparable or superior to reference drugs such as gentamicin and cycloheximide. Notably, analogue 8 showed the highest activity, with an inhibition zone of 45 mm and an MIC of 10.41 µg/mL against bacteria, and a zone of 61 mm with an MIC of 2.6 µg/mL against fungi. Molecular docking studies revealed that analogue 8 possessed the strongest binding affinities, while analogue 3 showed moderate interactions and analogue 7 displayed selective binding. Molecular dynamics simulations of analogue 7 confirmed stable ligand–protein interactions. ADME‐Tox predictions indicated favorable pharmacokinetic properties and low toxicity, supporting their potential as promising antimicrobial agents.