微波诱导的芳环亲核[18F]氟化反应：卤素对间位卤代（F、Cl、Br、I）苯甲腈衍生物[18F]氟取代反应的影响及合成
Microwave-induced nucleophilic [18F]fluorination on aromatic rings: synthesis and effect of halogen on [18F]fluoride substitution of meta-halo (F, Cl, Br, I)-benzonitrile derivatives.
作者信息
Guo Ning, Alagille David, Tamagnan Gilles, Price Ronald R, Baldwin Ronald M
机构信息
Department of Radiology & Radiological Sciences, Vanderbilt University School of Medicine, 1161 21st Avenue South, Nashville, TN 37232, USA.
出版信息
Appl Radiat Isot. 2008 Oct;66(10):1396-402. doi: 10.1016/j.apradiso.2008.03.003. Epub 2008 Mar 10.
Abstract
The meta-halo-3-methylbenzonitrile derivatives (-F, -Cl, -Br, -I) were synthesized as model compounds to study reactivity towards aromatic nucleophilic substitution. A single-mode microwave system was incorporated into a commercial radiochemical synthetic module for (18)F labeling. Labeling yields of 64% for fluoro-, 13% for bromo- and 9% for chloro-precursors were achieved in DMSO in <3 min. The observed order of reactivity of the leaving groups toward aromatic nucleophilic substitution was F>>Br>Cl>>>I.
摘要
合成了间卤代-3-甲基苯腈衍生物（-F、-Cl、-Br、-I）作为模型化合物，以研究其对芳香亲核取代反应的活性。将单模微波系统集成到用于（18）F标记的商业放射化学合成模块中。在二甲基亚砜中，<3分钟内氟代前体的标记产率为64%，溴代前体为13%，氯代前体为9%。观察到离去基团对芳香亲核取代反应的活性顺序为F>>Br>Cl>>>I。
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3
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J Med Chem. 2006 Feb 23;49(4):1466-74. doi: 10.1021/jm0509344.
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J Med Chem. 2005 Sep 8;48(18):5813-22. doi: 10.1021/jm0502743.
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Mol Imaging Biol. 2005 Jul-Aug;7(4):314-23. doi: 10.1007/s11307-005-0005-4.
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Bioorg Med Chem. 2005 Nov 15;13(22):6195-205. doi: 10.1016/j.bmc.2005.06.033. Epub 2005 Jul 27.
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