Synthesis and antitumor properties of some isoindolylalkylphosphonium salts

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Abstract
Antitumor evaluation of 2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyltriphenylphosphonium bromide revealed significant activity in [mouse] P-388 lymphocytic leukemia. As a follow-up to this chemical lead, a series of closely related phosphonium salts was prepared in which the 1,3-dihydro-1,3-dioxo-2H-isoindole ring system was maintained or in which it was replaced by other moieties such as maleimido, bromo, methoxy and isoindoline. Syntheses generally involved treatment of the appropriate N-(bromoalkyl)phthalimide with the required phosphine or condensation of the K salt of the substituted imide with .beta.-(bromoethyl)triphenylphosphonium bromide. From the biological data obtained for these compounds, several requirements can be defined for substantial antileukemic activity. Of utmost importance is the presence of triarylphosphonium halide moiety, coupled to an alkyl chain of 2 or 3 C atoms. The preferred terminus of the alkyl chain is the 1,3-dihydro-1,3-dioxo-2H isoindole ring system, although the observed activity of .beta.-(bromoethyl)triphenylphosphonium bromide would suggest that a superior carrier molecule could be developed.

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