We synthesized a series of new azo-based sulfonamides 8a-l via multistep chemical processes including chlorosulfonation, nucleophilic substitution, diazotization, and coupling reactions. The synthesized compounds were characterized using various physical and spectral techniques such as melting point, IR, 1H- and 13C-NMR, Mass, and elemental analysis. We evaluated the antibacterial and anticancer activities of compounds 8a-l. The cytotoxicity of these compounds was assessed on the MCF-7 breast cancer cell line and the MCF-10 human normal cell line after 48 h exposure. Notably, compound 8h demonstrated significantly higher cytotoxicity against MCF-7 (IC50 = 0.21 µM) while showing minimal toxicity towards the MCF-10 human normal cell line. To gain insights into the molecular interactions, we utilized molecular docking to predict the binding affinity of these compounds to the FGFR2 kinase receptor structure (PDB ID: 4J98). Compound 8h exhibited the highest docking score, consistent with our experimental results and demonstrating favorable protein-substrate interactions. In addition, we performed ADME prediction of the compounds, indicating their potential as lead drug candidates. Furthermore, we evaluated the antibacterial activity of compounds 8a-l against Gram-positive and Gram-negative bacteria. Compound 8i showed the strongest antibacterial activity against Staphylococcus aureus, a Gram-positive pathogen. This study provides valuable insights into the biological activities of azo-based sulfonamide derivatives, establishing their potential as both anticancer agents and antibacterial compounds.
