Collect. Czech. Chem. Commun. 1982, 47, 304-314

Syntheses and antineoplastic effects of some N-substituted imides of 1-substituted 4-aryl-naphthalene-2,3-dicarboxylic acids

Jiří Křepelka, Iva Vančurová, Jiří Holubek, Jiří Roubík and Drahuše Vlčková

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


Condensation of anhydrides Ia-d with primary amines, 2-hydroxyethylamine or formamide gave imides III-XXII. The formation of N-(2-hydroxyethyl)imides was accompanied by replacement of the aromatic hydroxy group at position 1 by a 2-hydroxyethylamine residue (XX, XXII. Reaction of the imides XIX and XX with thionyl chloride produced the corresponding 2-chloroethyl derivatives XXIII and XXIV. Alkylation of the imide II, or its alkali salt prepared in situ, by ethyl bromacetate in a homogenous medium or by 2-(N,N-diethylamino)ethyl chloride in a biphasic medium, gave the imides XXV and XXVI, respectively. Condensation of the anhydrides Ia and/or Id with 1,2-diaminobenzene gave the respective imides XIII and XIV, and pentacyclic derivatives of 12H-benz(f)isoindole[2,1-a]benzimidazole-12-one (XXVII and XXVIII, respectively) as mixtures of positional isomers. In biological evaluation for antineoplastic efficiacy in animals with experimental tumours the imide XX proved to have the widest range of application.