Stéen E Johanna L, Shalgunov Vladimir, Denk Christoph, Mikula Hannes, Kjær Andreas, Kristensen Jesper L, Herth Matthias M
Department of Drug Design and Pharmacology University of Copenhagen Universitetsparken 2 DK-2100 Copenhagen Denmark.
Department of Clinical Physiology Nuclear Medicine and PET University Hospital Copenhagen Copenhagen Denmark.
European J Org Chem. 2019 Feb 28;2019(8):1722-1725. doi: 10.1002/ejoc.201801457. Epub 2019 Jan 22.
Fluorine-18 possesses outstanding decay characteristics for positron emission tomography (PET) imaging. Therefore, it is ideally suited for clinical applications. As such, improved strategies to incorporate fluorine-18 into bioactive molecules are of utmost importance. Indirect F-labeling with amino-functionalized synthons is a convenient and versatile approach to synthesize a broad variety of PET tracers. Herein, we report a method to convert F-labeled azides to primary amines by means of the Staudinger reduction. Aliphatic and aromatic F-labeled azides were converted into the corresponding amines with high conversion yields. The method was easily automated. From a broader perspective, the applied strategy results in two useful synthons from a single precursor and thus increases the flexibility to label diverse chemical scaffolds with minimal synthetic effort.
氟-18在正电子发射断层扫描（PET）成像方面具有出色的衰变特性。因此，它非常适合临床应用。正因如此，将氟-18纳入生物活性分子的改进策略至关重要。用氨基官能化合成子进行间接氟标记是合成多种PET示踪剂的便捷且通用的方法。在此，我们报告一种通过施陶丁格还原将氟标记的叠氮化物转化为伯胺的方法。脂肪族和芳香族氟标记的叠氮化物以高转化率转化为相应的胺。该方法易于自动化。从更广泛的角度来看，所应用的策略从单一前体产生两种有用的合成子，从而以最小的合成工作量提高了标记不同化学支架的灵活性。
