We successfully synthesized 3 sets of new ursolic acid-based molecular hybrids using optimized reaction conditions and protocols, yielding satisfactory results. Series 8 and 9, where modifications were made at both C-3 and C-28 positions, were synthesized via click chemistry under microwave irradiation in the presence of sodium ascorbate and copper sulfate, yielding between 59% and 82%. Conversely, compounds 18a–f were synthesized with yields ranging from 71% to 99% by alkylating UA and secondary amines under basic conditions in the presence of K2CO3 in DMF at room temperature. Notably, compounds 9a, 18b, 18c, and 18d exhibited promising anticancer activity against breast cancer, while compounds 8a, 8c, 9a, and 18b–d demonstrated significant activity against bladder cell lines. These compounds’ calculated selectivity indexes (SIs) and their predicted molecular targets warrant further investigation, with compound 18d emerging as a lead candidate. Importantly, these compounds’ toxicity and pharmacokinetics profiles fall within acceptable limits for drug development purposes. Newly synthesized compounds have demonstrated potential anticancer drug-like properties, though the underlying mechanism remains unclear and requires further investigation. These results represent a valuable contribution to developing novel anticancer drug candidates.