Synthesis, Computational, and Photophysical Probing Studies on Mono-Azo Sulfonamides, and Their Antibacterial Activity

Objective: Novel azo-linked substituted sulfonamides were synthesized via diazo coupling with the molecular formula (C9H10N4O2S2, C11H11N3O2S) and characterized by FT-IR, UV-vis, HR-MS, and 1H NMR spectroscopy techniques. The photophysical studies were carried out using experimental techniques. Absorption and fluorescence maxima of all the synthesized molecules were determined by using different solvents. Our synthesized mono-azo derivatives are interested in identifying the cellular target site for sulfonamides (F1-F2) and (P1-P2). The newly synthesized compounds were examined for their in vitro antibacterial activity against Staphylococcus aureus and Escherichia coli strains. Methods: In this study, we focused on the sulfonamide architecture. Antibacterial activity of compound (F1), (F2), (P1), and (P2) derivatives was studied by measuring the diameter of the inhibition zone, using the Disc-agar diffusion method. Results and Discussion: Density functional theory was used to demonstrate the electronic and optical properties of the synthesized molecules. In the correlation between the HOMO–LUMO energy gap, the derivative (F1) shows a higher (3.9866 eV) and (F2) shows a lower (3.2063 eV) excitation energy. The synthesized compound (F1) looks into antibacterial activity, exhibited more zone inhibition 25 mm in the concentration 75 µL/mL in gram-negative bacteria when compared with the common antibiotic Ciprofloxacin. Additionally, the results emerged from the in silico molecular docking studies the compound (F2) showed highest binding energy against cyclin-dependent kinase (ΔGb = –9.8 kcal/mol). Conclusions: The synthesized four mono-azo sulfonamide derivatives (F1), (F2), (P1), and (P2) are reported in photophysical, CDFT, antibacterial, and molecular docking studies with relevant results.