As part of the valorization of agricultural waste into bioactive compounds, a series of structurally novel oleanolic acid ((3β-hydroxyolean-12-en-28-oic acid,OA-1)-phtalimidines (isoindolinones) conjugates18a–ubearing 1,2,3-triazole moieties were designed and synthesized by treating an azide4previously prepared fromOA-1isolated from olive pomace (Olea europaeaL.) with a wide range of propargylated phtalimidines using the Cu(I)-catalyzed click chemistry approach.OA-1and its newly prepared analogues,18a–u,were screened in vitro for their antibacterial activity against two Gram-positive bacteria,Staphylococcus aureusandListeria monocytogenes, and two Gram-negative bacteria,Salmonella thyphimuriumandPseudomonas aeruginosa. Attractive results were obtained, notably againstL. monocytogenes. Compounds18d,18g, and18hexhibited the highest antibacterial activity when compared withOA-1and other compounds in the series against tested pathogenic bacterial strains. A molecular docking study was performed to explore the binding mode of the most active derivatives into the active site of the ABC substrate-binding protein Lmo0181 fromL. monocytogenes. Results showed the importance of both hydrogen bonding and hydrophobic interactions with the target protein and are in favor of the experimental data.