A series of novel benzophenone-derived novel azo dyes (3c–3d) were successfully synthesized through diazotization–coupling reactions and characterized using UV–visible, FTIR, ¹H NMR, ¹³C NMR, and LC–MS spectral analyses. The biological potential of the synthesized compounds was investigated through molecular docking and in vitro cytotoxic evaluation against HepG2 liver carcinoma cells. Docking studies revealed favourable ligand– protein interactions, with compound 3d exhibiting the highest binding affinity (−6.608 kcal/mol). MTT assay results demonstrated that compound 3d possessed significant cytotoxic activity with an IC₅₀ value of 40.65 µg/mL, whereas compound 3c showed comparatively lower activity (IC₅₀ =
178.88 µg/mL). The observed cytotoxic response correlated well with the molecular docking results. The present study demonstrates the potential of benzophenone-based azo compounds as biologically active molecules with notable anticancer potential