A series of N-(naphthalene-2-yl)-3-(substituted phenyl) prop-2-enamides were synthesized by reaction of β -acetyl amino naphthalene with substituted aromatic aldehydes in presence of absolute ethanol and 30% NaOH. The intermediate β-acetyl amino naphthalene was prepared by refluxing β-amino naphthalene with acetic anhydride and glacial acetic acid. A total of nine compounds were synthesized, purified and characterized on the basis of their spectral data. The title compounds were screened for anti-inflammatory activity by carrageenan induced rat hind paw method and antioxidant activity by using nitric oxide scavenging activity and reduction of stable free DPPH. Among the series of compounds 4-methoxy (3) and 4-dimethyl amino (6) derivatives exhibited significant antiinflammatory activity. Among the test compounds 4-dimethyl amino (6) and 4-isopropyl (7) derivatives exhibited good antioxidant activity in both nitric oxide (NO) scavenging activity and reduction of stable free radical DPPH.