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A series of new 2-substituted-N-(1,3-thiazole-2-yl)acetamide 3–7 and N-(benzo[d]thiazol-2-yl)-2-(substituted)acetamide 10–13 derivatives have been synthesized and evaluated in vivo (rat paw edema) for their anti-inflammatory activities and in silico(docking studies) to recognize the hypothetical binding motif of the title compounds with the cyclooxygenase isoenzyme (COX-2) employing GLIDE software (Schrodinger Inc.). The compounds, 10–13 were found to have good anti-inflammatory activities [around 84–93 % of the standard: indomethacin]. The binding mode of the title compounds has been proposed based on the docking studies. Further, the predicted ADME properties of all the tested compounds were found to be in the ranges as predicted by QikProp for 95 % of known oral drugs and also satisfy the Lipinski’s rule of five.