1335316-95-4Relevant academic research and scientific papers
Single-step syntheses of no-carrier-added functionalized [ 18F]fluoroarenes as labeling synthons from diaryliodonium salts
Chun, Joong-Hyun,Pike, Victor W.
, p. 6300 - 6306 (2013/09/23)
Radiotracers labelled with short-lived fluorine-18 (t1/2 = 109.7 min) are keenly sought for biomedical imaging with positron emission tomography (PET). The radiotracers are mostly required at high specific radioactivities, necessitating their radiosyntheses from cyclotron-produced no-carrier-added [18F]fluoride ion. PET radiotracers encompass wide structural diversity and molecular weight. Hence, diverse 18F-labeling methodology is needed to accomplish the required radiosyntheses in a simple and rapid manner. A useful strategy is to introduce nucleophilic [ 18F]fluoride ion first into a labeling synthon that may then be applied to label the target radiotracer. Here, we show that various functionalized [18F]fluoroarenes may be rapidly synthesized as labeling synthons through single-step reactions of appropriate diaryliodonium salts with [18F]fluoride ion. Decay-corrected radiochemical yields (RCYs) varied with position of functional group, choice of electron-rich aryl ring in the diaryliodonium salt, and choice of anion. Under best conditions, 18F-labeled fluorobenzaldehydes, fluorobenzyl halides, fluorobenzoic acid esters and fluorophenyl ketones were obtained selectively in 40-73%, 20-55%, 46-89% and 81-98% RCYs, respectively. This versatile straightforward methodology will enhance the scope for producing structurally complex, yet useful, PET radiotracers.
Syntheses of meta-[18F]fluorobenzaldehyde and meta-[ 18F]fluorobenzylbromide from phenyl(3-Formylphenyl) iodonium salt precursors
Basuli, Falguni,Wu, Haitao,Griffiths, Gary L.
, p. 224 - 228 (2012/05/20)
18F-labeled fluorobenzaldehydes and fluorobenzylbromides are useful synthons for the preparation of positron emission tomography radiopharmaceuticals. Although ortho- and para-[18F] fluorobenzaldehydes can easily be prepared with high yields, the corresponding meta-derivatives are more problematic. In order to improve the yield of meta-[18F]fluorobenzaldehyde, we used the corresponding diaryliodonium salt precursors, since diaryliodonium salts had already been used as precursors in the preparations of 18F-labeled electron-rich, as well as electron-deficient, aromatic rings. Diaryliodonium salts with different counter ions [PhIPhCHO]X (X = Cl, Br, OTs, OTf) were synthesized. 18F radiolabeling was performed using different bases at different temperatures in the presence of a radical scavenger, 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO). The best conversion (～80%) to meta-[18F] fluorobenzaldehyde was obtained using CsHCO3 base at a reaction temperature of 110°C. To study iodonium salt counter ion effects on radiofluorination, each precursor was separately treated with Cs[ 18F]F/CsHCO3 in DMF at 110°C for 5 min in the presence of TEMPO. Our observed reactivity order was OTs18F]fluorobenzaldehyde thus obtained was reduced to the corresponding alcohol with aqueous NaBH4 at room temperature and then converted to meta-[18F]fluorobenzylbromide using triphenylphosphine dibromide. Formation of meta-[18F]fluorobenzylbromide was confirmed using high-performance liquid chromatography and the desired product was purified on a silica Sep-Pak plus cartridge. Copyright
A first synthesis of 18F-radiolabeled lapatinib: A potential tracer for positron emission tomographic imaging of ErbB1/ErbB2 tyrosine kinase activity
Basuli, Falguni,Wu, Haitao,Li, Changhui,Shi, Zhen-Dan,Sulima, Agnieszka,Griffiths, Gary L.
, p. 633 - 636 (2011/12/03)
Fluorine-18-labeled lapatinib has been successfully synthesized for the first time by the reaction of a dimethylformamide solution of meta-[ 18F]fluorobenzylbromide with a Boc-protected lapatinib precursor fragment. The reaction proceeded in th
