Ibuprofen, a 2-arylpropionic acid NSAID, is widely used to treat pain, fever, and inflammation but may causegastrointestinal ulcers, liver injury, and renal impairment on prolonged use. Ulcerogenicity is mainly due totheinteraction of its carboxylic acid group with the COX-1 enzyme, though this group is essential for activity. Inthisstudy, the carboxylic acid of Ibuprofen was modified into amide derivatives using 4-aminobenzoic acid, aminophenolic acids, and their esters. The designed molecules were synthesized and characterized by physical parameters and relevant spectral data. The synthesized derivatives were evaluated for their in vitro antioxidant properties by DPPH scavenging and nitric oxide free radical scavenging assays, and in vitro antiinflammatoryactivity by erythrocyte membrane stabilization and protein denaturation methods. The antioxidant studies (DPPHand nitric oxide scavenging) showed good radical scavenging activity for compounds 14, 17 and 18. In vitroantiinflammatory assays revealed that several derivatives, particularly 15, 18, and 19, exhibited significant membrane stabilization and protein denaturation inhibition comparable to Ibuprofen. Additionally, computational analysis was performed using Molinspiration, PASS analysis, and Osiris Property Explorer to assess drug-likeness, antiinflammatory potential, and toxicity properties respectively, for the synthesized compounds (9-20). In silicoADMET and toxicity predictions confirmed favorable drug likeness, good oral absorption, and low toxicity profiles. Overall, compound 18 emerged as the most promising lead, showing consistent performance across the biological assays. This study contributes to the development of safer NSAID derivatives. The findings provide a promisingframework for designing gastroprotective anti-inflammatory agents and support further optimization and invivoevaluation.