title: 2,3-Dimethyl-1,4-naphthoquinone derivatives as bioreductive alkylating agents with cross-linking potential.
abstract: 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.
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D051379:Mice; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000627:therapeutic use; D012510:Sarcoma 180 / Q000188:drug therapy
chemical_list: D000970:Antineoplastic Agents; D009285:Naphthoquinones; C041498:2,3-dimethyl-1,4-naphthoquinone