PMID: 11310603Apr 20, 2001Paper

Synthesis of high-specific-radioactivity 4- and 6-[18F]fluorometaraminol-PET tracers for the adrenergic nervous system of the heart

Bioorganic & Medicinal Chemistry
Oliver LangerC Crouzel

Abstract

Fluorine-18- (t(1/2) 109.8 min) and carbon-11 (t(1/2) 20.4 min)-labeled norepinephrine analogues have been found previously to be useful positron-emission-tomography (PET) radioligands to map adrenergic nerve terminals of the heart. Metaraminol ((1R,2S)-2-amino-1-(3-hydroxyphenyl)-1-propanol) is a metabolically stable structural analogue of norepinephrine and possesses high affinity towards the norepinephrine transporter and the vesicular monoamine transporter. This paper presents the radiosynthesis of new positron-emission-tomography halogeno analogues of metaraminol labeled with high specific radioactivity. Firstly, fluorine-18-labeled 4-fluorometaraminol (4-[18F]FMR or (1R,2S)-2-amino-1-(4-[18F]fluoro-3-hydroxyphenyl)-1-propanol) and its three other stereoisomers were prepared based on the following key steps: (a) condensation of the corresponding no-carrier-added labeled fluorobenzaldehyde with nitroethane, and (b) HPLC (C18 and chiral) resolution of the diastereomeric product mixture into the four individual enantiomers. Secondly, the corresponding 6-fluoro analogues, fluorine-18-labeled 6-fluorometaraminol (6-[18F]FMR or (1R,2S)-2-amino-1-(2-[18F]fluoro-5-hydroxyphenyl)-1-propanol) and its three other enantiomers, were pr...Continue Reading

References

Mar 1, 1990·Journal of Medicinal Chemistry·D M WielandP S Sherman
Feb 1, 1988·Journal of Medicinal Chemistry·S G MislankarS A Toorongian
Nov 1, 1968·Journal of Medicinal Chemistry·W S SaariE L Engelhardt
Jul 1, 1966·Acta Physiologica Scandinavica·A Carlsson, B Waldeck

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Citations

Oct 9, 2004·Journal of Nuclear Cardiology : Official Publication of the American Society of Nuclear Cardiology·Frank M Bengel, Markus Schwaiger
Sep 15, 2017·European Journal of Nuclear Medicine and Molecular Imaging·Ryohei KobayashiTakahiro Higuchi
May 29, 2012·Angewandte Chemie·Zhanghua GaoVéronique Gouverneur
Nov 29, 2013·Journal of Labelled Compounds & Radiopharmaceuticals·Fabian KüglerHeinz H Coenen
Jun 6, 2003·Journal of the American Chemical Society·Simon B Blakey, David W C MacMillan
May 29, 2009·Journal of Medicinal Chemistry·Delphine MénardCaroline J Springer
Jul 18, 2017·The Journal of Organic Chemistry·Jan Otevrel, Pavel Bobal
Jun 1, 2007·Journal of the American Chemical Society·Tobias L RossHeinz H Coenen

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