Details

Autor(en) / Beteiligte

• Rotteveel, Lonneke
• Poot, Alex J.
• Funke, Uta
• Pekošak, Aleksandra
• Filp, Ulrike
• Lammertsma, Adriaan A.
• Windhorst, Albert D.

Titel

Radiosynthesis of 1‐iodo‐2‐[11C]methylpropane and 2‐methyl‐1‐[11C]propanol and its application for alkylation reactions and C―C bond formation

Ist Teil von

• Journal of labelled compounds & radiopharmaceuticals, 2017-10, Vol.60 (12), p.566-576

Ort / Verlag

England: Wiley Subscription Services, Inc

Erscheinungsjahr

2017

Quelle

MEDLINE

Beschreibungen/Notizen

• The multitude of biologically active compounds requires the availability of a broad spectrum of radiolabeled synthons for the development of positron emission tomography (PET) tracers. The aim of this study was to synthesize 1‐iodo‐2‐[11C]methylpropane and 2‐methyl‐1‐[11C]propanol and investigate the use of these reagents in further radiosynthesis reactions. 2‐Methyl‐1‐[11C]propanol was obtained with an average radiochemical yield of 46 ± 6% d.c. and used with fluorobenzene as starting material. High conversion rates of 85 ± 4% d.c. could be observed with HPLC, but large precursor amounts (32 mg, 333 μmol) were needed. 1‐Iodo‐2‐[11C]methylpropane was synthesized with a radiochemical yield of 25 ± 7% d.c. and with a radiochemical purity of 78 ± 7% d.c. The labelling agent 1‐iodo‐2‐[11C]methylpropane was coupled to thiophenol, phenol and phenylmagnesium bromide. Average radiochemical conversions of 83% d.c. for thiophenol, 40% d.c. for phenol, and 60% d.c. for phenylmagnesium bromide were obtained. In addition, [11C]2‐methyl‐1‐propyl phenyl sulphide was isolated with a radiochemical yield of 5 ± 1% d.c. and a molar activity of 346 ± 113 GBq/μmol at the end of synthesis. Altogether, the syntheses of 1‐iodo‐2‐[11C]methylpropane and 2‐methyl‐1‐[11C]propanol were achieved and applied as proof of their applicability. In this paper, 4 model reactions were performed for the application of 2‐methyl‐1‐[11C]propanol and 1‐iodo‐2‐[11C]methylpropane in PET tracer development reactions. The labelling agent 1‐iodo‐2‐[11C]methylpropane was coupled to thiophenol (A), phenol (B), and phenylmagnesium bromide (D). In addition, 2‐methyl‐1‐[11C]propanol was coupled to fluorobenzene (C). These two radiolabelled synthons provide the opportunity to develop novel PET tracers that have been inaccessible so far.