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Schiff bases derived from p-aminobenzyl alcohol as trigger groups for pH-dependent prodrug activation

2010; Elsevier BV; Volume: 51; Issue: 33 Linguagem: Inglês

10.1016/j.tetlet.2010.06.055

1873-3581

Ivonne A. Müller, Felix Kratz, Manfred Jung, André Warnecke,

Chemical Synthesis and Analysis

A number of novel acid-sensitive Schiff bases derived from p-aminobenzyl alcohol and various benzaldehyde derivatives were synthesized and were subsequently shown to trigger benzyl elimination reactions. The kinetics of acid-catalyzed hydrolysis at pH 5.0 as well as stability at pH 7.4 were studied using fluorogenic model compounds. Two fluoro-substituted Schiff bases showed efficient hydrolysis at pH 5.0 combined with a long-term stability at pH 7.4 and are considered suitable candidates for the development of anticancer prodrugs.