A series of newly naphthoquinone derivatives were synthesized using 2,3-dihydro-2,3-epoxy-1,4-naphthoquinone (1) as a starting material. The corresponding acetophenyl derivative 7 was used as building blocks for synthesis of different heterocycles incorporated naphthoquinone moiety. The newly synthesized compounds were characterized utilizing the corresponding analytical and spectroscopic data and evaluated as antioxidant activity by superoxide (NBT) free radical scavenging methods. Compounds 21, 22 promosing the more potent antioxidant agents than ascorbic acid. Moreover, the newly synthesized quinones were tested for their Cytotoxicity by brine shrimp lethality bioassay. Quinone derivatives 3, 12, 18, 23 were proven to be the best potent cytotoxic agents.