Faculty of Chemistry, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland.
Eur J Med Chem. 2012 Jun;52:184-92. doi: 10.1016/j.ejmech.2012.03.017. Epub 2012 Mar 17.
A hexadentate ligand built on an amine-bis(phenol) skeleton with an aminal, self-immolative moiety is presented. Synthesis of the ligand is convenient and relatively high yielded. Moreover, it enables synthesis of many derivatives, both in the amino-phenol and aminal fragment (various heterocycles). Once the final hexadentate ligand is synthesized via the Katritzky reaction, it becomes prone to hydrolysis. Bioactivation by β-galactosidase cleaves the glycosylic bond and a spontaneous collapse of the aminal fragment occurs, thus leading to a pentadentate chelate. This bioactivation has been shown for pyrazole, 1,2,4-triazole and benzotriazole derivatives.
本文介绍了一种基于胺-双（苯酚）骨架的具有亚胺、自毁部分的六齿配体。该配体的合成方便，产率较高。此外，它还可以合成许多衍生物，包括氨基-苯酚和亚胺片段（各种杂环）。一旦通过 Katritzky 反应合成了最终的六齿配体，它就容易发生水解。β-半乳糖苷酶的生物活化作用会切断糖苷键，亚胺片段会自发坍塌，从而形成五齿螯合物。这种生物活化作用已经在吡唑、1,2,4-三唑和苯并三唑衍生物中得到了证明。
