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Bioreducible 2,3-disubstituted 1,4-naphthoquinones have been synthesized and evaluated for anticancer activity by measuring their capacity to prolong the life span of Sarcoma 180 tumor bearing mice. The leaving group in the 2- and 3-positions of these agents significantly influenced the degree of antineoplastic activity, with the most active agents being the methyl sulfonate (5), the methyl carbamate (9), and the 2-chloroethyl carbamate (10) derivatives; when these quinones were administered daily for 6 consecutive days, they produced maximum T/C X 100 values of 232, 266, and 230, respectively.
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