Herein, oleic acid was derivatized to 1,2,3-triazolyl oleate esters through propargylation followed by copper(I)-mediated azide-alkyne [3 + 2] cycloaddition, confirmed by IR, NMR and HRMS. All products exhibited similar antioxidant activity to oleic acid. The products demonstrated antibacterial activity at 10 mg/mL. Compound 4d was identified as the most potent cytotoxic agent, showing 34.31 % inhibition at 200 μM against the MCF-7. Additionally, 4d displayed 15.85 % inhibition of shikimate kinase at 0.5 mg/mL. Thus, these modified compounds exhibit better activity compared to oleic acid, making this series a promising candidate for drug discovery and development. © 2024 The Authors