In this work, a series of piperazine substituted indole derivatives were synthesized and evaluated for their in vitro antioxidant and anti-inflammatory activities. The results of antioxidant activity showed that compounds 2 (81.63%) and 11 (85.63%) had comparable DPPH free radical scavenging activity to Vit E (88.6%). The in vitro antiinflammatory assays indicated that most of the compounds had more higher anti-inflammatory activities than standart ASA. Docking results revealed that compound 11 possessing the strongest anti-inflammatory activities showed the Hbond interactions with the key residues of COX-2 active site. It suggested that the anti-inflammatory activity of the compounds might result from COX-2 inhibition. It will be verified with further enzyme inhibition assays. [ABSTRACT FROM AUTHOR]