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- W2274656990 abstract "185 Objectives In 18F-chemistry of radiopharmaceuticals aromatic amines are of considerable interest. Besides their use as prostethic groups, they are important structure motifs for a variety of bioactive small molecules. Here we report an efficient way to generate n.c.a. 3-[18F]fluorobenzylamine, 4-[18F]fluoroaniline and 1-(4-[18F]fluorophenyl)piperazine which in general are difficult to access. Starting from the latter the highly selective dopamine D4 agonist [18F]FAUC 316 was synthesized. Methods In order to facilitate the radiosynthesis of complex pharmaceuticals various new iodonium salts and ylides based on para-iodo, meta-cyano and para-acetamide derivatives of simple arenes were developed for their use as radiosynthons. Their 18F-labeling yields were compared using DMF, DMSO and MeCN as solvent under conventional heating between 80 and 130°C. While 18F-fluorinated cyano and acetamide derivatives were cleaved to the corresponding primary amines, 4-[18F]fluoroiodobenzene was transferred to the tertiary arylamine in a one-pot synthesis. One additional step led to potent radiopharmaceuticals like the receptor ligand [18F]FAUC 316 which was evaluated for specific binding by in vitro competition experiments. Results Iodonium ylides showed distinct higher radiochemical yields than corresponding iodonium salts of up to 70% with the additional advantage of a broad choice of solvents. Thus one-pot syntheses were achievable with low product losses. Especially amine cross-coupling conditions in polar media were optimized reaching 70-90% conversion yields. From this in a third step [18F]FAUC 316 was synthesized in overall radiochemical yields of 18% after HPLC separation. In vitro evaluation showed a competition of only 10% using internal D4 standards. Conclusions The new precursor class of iodonium ylides and the one-pot cross-coupling in polar media lead to 18F-labeled aromatic amines in high yields and short reaction time. The high overall radiochemical yield of the challenging radioligand [18F]FAUC 316 demonstrates the efficiency of the developed methods" @default.
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- W2274656990 date "2012-05-01" @default.
- W2274656990 modified "2023-09-23" @default.
- W2274656990 title "Efficient radiosyntheses of 18F-fluorinated aromatic amines using innovative iodonium precursors" @default.
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