Abstract
Although N-Mannich bases of amides, imides, hydantoins and various other NH-acidic compounds have been known for a long time, and several drug substances and other compounds bearing an NH-acidic group have been modified by N-aminomethylation and tested as potential medicinal agents, the facile decomposition of several N-Mannich bases in aqueous solution has not been generally recognized. In this paper recent kinetic studies by the authors on the stability of a great number of N-Mannich bases are summarized and used to show that several previous reports on biological testing of various N-Mannich bases may be unrealistic because of very rapid decomposition of the derivatives in aqueous medium. The structural factors influencing the decomposition rate of N-Mannich bases are discussed and structure-reactivity relationships are given which may be useful for the prediction of stability of new N-Mannich bases as well as for retrospective evaluations.
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