In the present investigation we have synthesized a series of new 2-arylidene-N-(benzoxazole-2-yl) hydrazine carboxamide and 2-arylidene-N-(5-chloro benzoxazole-2-yl) hydrazine carboxamide derivatives (VIIIa-VIIIf& VIIIA-VIIIE). The newly synthesized derivatives were characterized by using the data of IR, 'H NMR and Mass Spectral analysis. Thus synthesized and characterized targeted compounds were further screened for their anti-inflammatory activity by using Carrageenan - induced paw edema rat model. Among all the newly synthesized derivatives, Compounds VIIIa-c and Compounds VIIIA-C were reduced the inflammation very significantly , thus these compounds showed promising anti-inflammatory activity and compounds VIIId-VIIIf& VIIID-VIIIF showed moderate anti-inflammatory activity.