4.4 Article

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

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 33, Pages 4371-4374

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.06.055

Keywords

Prodrug activation; Acid-sensitive; Benzyl elimination; Schiff base

Funding

  1. Deutsche Forschungsgemeinschaft (DFG)

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A number of novel acid-sensitive Schiff bases derived horn p-aminobenzyl alcohol and various benzaldehyde derivatives were synthesized and were subsequently shown to trigger benzyl elimination reactions The kinetics of acid-catalyzed hydiolysis at pH 50 as well as stability at pH 74 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 74 and are considered suitable candidates for the development of anticancer prodrugs (c) 2010 Elsevier Ltd All lights reserved

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