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The synthesis of 4‐(4‐([ 11 C]methoxyphenyl) ‐(5‐fluoro‐2‐hydro‐xyphenyl)‐methylene‐aminobutyric acid, as a potential radioli‐gand for the gaba receptor in the brain
Author(s) -
Vos Filip De,
Slegers Guido
Publication year - 1994
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580340708
Subject(s) - chemistry , radiosynthesis , demethylation , methylene , high performance liquid chromatography , yield (engineering) , radioligand , nuclear chemistry , medicinal chemistry , radiochemistry , chromatography , receptor , in vivo , biochemistry , gene expression , materials science , microbiology and biotechnology , gene , metallurgy , dna methylation , biology
Abstract A procedure for the synthesis of 4‐(4‐[ 11 C]methoxyphenyl) ‐(5‐fluoro‐2‐hydroxyphenyl)‐methylene‐aminobutyric acid has been developed. The production entailed a O‐methylation of 5‐fluoro‐2‐hydroxy‐4′‐hydroxybenzophenone with cyclotron produced [ 11 C]iodomethane in the presence of alkali and a subsequent Schiff reaction of 5‐fluoro‐2‐hydroxy‐4′‐( 11 C]methoxybenzophenone with γ‐aminobutyric acid. 5‐Fluoro‐2‐hydroxy‐4′‐hydroxybenzophenone was obtained by a demethylation of the 4′‐methoxyderivative with boron tribromide. Subsequent purification by HPLC and sterilisation by filtration gave 740 MBq (20 mCi) of an injectable solution. The radiochemical yield (decaycorrected) from [ 11 C]iodomethane achieved 27%. The specific activity was 3.7 GBq/μmol (100 mCi/μmol) at the end of the radiosynthesis (45 min from EOB). The preparations have been demonstrated to be chemically and radiochemically pure by HPLC and TLC.