Synthesis of fluorine-18 labeled GABA uptake inhibitors.
The first syntheses of fluorine-18 labeled inhibitors of GABA reuptake [(R,S)-1-[2-[4-[18F]fluorophenyl]phenyl]methoxyethyl]piperidine- 3-carboxylic acid, (R,S)-1-[2-[(4-[18F]trifluoromethyl)phenyl][(4- trifluoromethyl)phenyl]-methoxyethyl]piperidine-3-carboxylic acid] are described. These N-substituted nipecotic acid derivatives were prepared in no-carrier-added form by the condensation of the appropriately substituted [18F]benzhydryl chlorides (prepared in three steps from [18F]fluoride ion) with N-(2-hydroxyethyl)nipecotic acid ethyl ester, followed by ester hydrolysis. Overall radiochemical yields were 17-28% (corrected, 150 min synthesis time). A simple new method for synthesis of a [18F]trifluoromethyl group by the nucleophilic substitution of a bromodifluoromethyl substituent has also been developed.
Kilbourn
M R
MR
Division of Nuclear Medicine, University of Michigan, Ann Arbor.
Pavia
M R
MR
Gregor
V E
VE
D005462:Fluorine Radioisotopes; D014179:Neurotransmitter Uptake Inhibitors / Q000138:chemical synthesis*; D005680:gamma-Aminobutyric Acid / Q000378:metabolism*
D005462:Fluorine Radioisotopes; D014179:Neurotransmitter Uptake Inhibitors; D005680:gamma-Aminobutyric Acid