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Some novel benzoquinones and their dimethoxy chemical precursors were synthesized based on shikonin structural features. The quinone functionality showed strong .OH radical scavenging, whereas benzoquinones with an α- hydroxy-containing saturated side chain exhibited increased soybean lipoxygenase inhibition. Compounds 5, 5b and 7 were superior to indomethacin in vivo in the carrageenin-induced rat paw edema inhibition.