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With the aim of obtaining new antitumor drugs more active than previously described 5, 8-quinazolinediones, a series of dimers of 5, 8-quinazolinediones linked in the 4-position by a simple or a substituted χ, ω-diaminopolymethylenic chain was studied. The structure-activity relationships of these compounds are discussed as functions of the length of the chain, presence or absence of other functional groups, nature of these functional groups, position of the chain and nature of the substituents in the 6 and (or) 7-positions. When bis (5, 8-quinazolinediones) were substituted in the 6-position with a methoxyl group, the dimerization showed a variable effect on cytotoxicity toward L 1210 leukemia cells. Bis [4-amino-bis-6, 7 (1-aziridinyl)-5, 8-quinazolinediones] which exhibited high cytotoxic activity (IC50 0.0037 to 0.018μm) were further screened in vivo for activity against murine P388 leukemia. Antitumor activity was increased by the dimerization of the molecule. The most potent compound bears an additional tertiary amino function on the chain.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Heterocyclic quinones. XIII. Dimerization in the series of 5,8-quinazolinediones: Synthesis and antitumor effects of bis(4-amino-5,8-quinazolinediones).