A series of newer 3-(4'-methoxyphenyl)-5-substituted phenylisoxazoles derivatives have been synthesized by reacting hydroxylamine hydrochloride with chalcone. The chalcones were formed by reacting different aromatic aldehydes with 4-methoxyacetophenone in presence of aqueos KOH. The acute toxicity study was carried on all the synthesized compounds and they were screened for their anti-inflammatory activity by carrageenan induced paw edema method. Anti-inflammatory studies showed statistically significant activity when compared to control indomethacin. The two most potent compounds giving good anti-inflammatory activity were further evaluated for their anti-ulcer activity. The compounds were subjected to docking and quantitative structure activity relationships (QSAR) studies.