Triazenes of Phenylbutyric, Hydrocinnamic, Phenoxyacetic, and Benzoylglutamic Acid Derivatives

Abstract

p-Dialkyltriazeno derivatives of the ethyl esters and acid hydrazides of phenylbutyric, hydrocinnamic, phenoxyacetic, and benzoylglutamic acids were synthesized. The triazenophenylbutyric acid derivatives are structurally related to chlorambucil, and the hydrocinnamic and phenoxyacetic acid derivatives are related to other antineoplastic aromatic nitrogen mustards. All of the triazeno groups contained unsubstituted alkyl groups (except for a hydroxyethyl group in a derivative of benzoylglutamic acid). In initial tests of these compounds versusmouse lymphatic leukemia L-1210, ethyl p-(3-butyl-3-methyl-1-triazeno)hydrocinnamate (VIb) was the most effective compound in increasing the survival time of treated animals. Certain other hydrocinnamic and phenylbutyric acid derivatives caused small increases in survival time.