anticancer drug, dibenzodioxin, oxanthrene, tricyclic carboxamide

Authors: Spicer A.; Denny A.

Source: Anti-Cancer Drug Design, Volume 15, Number 6, 2000 , pp. 453-458(6)

Publisher: Cognizant Communication Corporation

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Abstract:

We report the synthesis of five new tetracyclic benzodioxins, from reaction of 1,2-naphthalenediol, 7,8-dihydroxyquinoline or 7,8-dihydroxyisoquinoline with isopropyl 2-chloro-3-nitrobenzoate. Mixtures of isomeric esters were obtained which were separated by conventional flash silica chromatography or preparative HPLC and fully characterized by NMR. Ester hydrolysis and amide formation afforded the target carboxamides 7-9, 11 and 12. The biological activities of the benzodioxins broadly paralleled those of the corresponding phenazines. A tetracyclic pyrido derivative was the most cytotoxic, with an IC₅₀ of 0.11 [mgr]M in P388 leukaemia cell culture, but did not represent a significant improvement over a number of 9-substituted tricyclic phenazines.

Keywords: anticancer drug, dibenzodioxin, oxanthrene, tricyclic carboxamide

Document Type: Research article

Publication date: 2000-12-01