Efficient synthesis of [¹⁸F]FPyME: A new approach for the preparation of maleimide-containing prosthetic groups for the conjugation with thiols

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• 作者：Melanie Cavani ; Dirk Bier ; Marcus Holschbach and Heinz H. Coenen
• 刊名：Journal of Labelled Compounds and Radiopharmaceuticals
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：60
• 期：1
• 页码：87-92
• 全文大小：730K
• ISSN：1099-1344

文摘

An improved high yielding radiosynthesis of the known thiol-reactive maleimide-containing prosthetic group1-[3-(2-[¹⁸F]fluoropyridine-3-yloxy)propyl]pyrrole-2,5-dione ([¹⁸F]FPyME) is described. The target compound was obtained by a two-step one-pot procedure starting from a maleimide-containing nitro-precursor that was protected as a Diels-Alder adduct with 2,5-dimethylfurane. Nucleophilic radiofluorination followed by heat induced deprotection through a Retro Diels Alder reaction yielded, after chromatographic isolation, [¹⁸F]FPyME with a radiochemical yield of 20% in about 60 min overall synthesis time. A variety of other [¹⁸F]fluoropyridine based maleimide-containing prosthetic groups should be accessible via the described synthetic strategy.