Some new structural variants of the alkaloid carbazoquinocin C were synthesized in a few steps with good to excellent yields. The key step comprises a cyclisation reaction of appropriate 2-vinylindoles with oxalyl chloride. The carbazole-3,4-quinones are able to trap oxygen-centred radicals. In some biological/biochemical assays some of these compounds exhibit extraordinary results including inhibition of cyclooxygenase-1 and 5-lipoxygenase in the μM-range. Moreover some of the carbazoquinocin C-variants inhibit significant oxidative damage of cellular DNA in nM-range.