A novel series of isatin incorporating an oxazole moiety were synthesized to explore their potential biological significance. The target compounds were obtained through a synthetic pathway involving the condensation reaction. The synthesized molecules were structurally characterized using various spectroscopic techniques including FT-IR, NMR and mass spectrometry, confirming the formation of the desired frameworks. Molecular docking studies were performed to evaluate the binding interactions of the synthesized compounds with the selected biological target associated with anticancer activity. The docking results revealed favorable binding affinities and significant interactions such as hydrogen bonding, π–π stacking, and hydrophobic interactions within the active site of the receptor.