2-Substituted 8-propargyloxyquinoline derivatives have been synthesized from 2-substituted-8-hydroxyquinolines by O-propargylation method (30%-98% yields). The newly synthesized compounds were tested for in vitro antioxidant activities such as DPPH radical scavenging, ferrous chelating, and reducing power activities. The maximum radical scavenging (46.5%) and reducing power activities were obtained from 1 and maximum ferrous chelating effect was obtained from 6 (72.1%) at the concentration of 500 mu g/mL. To indicate DNA binding activity of the complexes calf thymus DNA was used. The compounds were also evaluated for their antimicrobial activity against three gram-positive and three gram-negative bacteria. Compounds 3 and 5 exhibited antibacterial activity against all tested gram-positive bacteria.