Reference : Synthesis of (R)-(-)- and (S)-(+)-4-fluorodeprenyl and (R)-(-)- and (S)-(+)-[N-11C-me...
Scientific journals : Article
Human health sciences : Radiology, nuclear medicine & imaging
Synthesis of (R)-(-)- and (S)-(+)-4-fluorodeprenyl and (R)-(-)- and (S)-(+)-[N-11C-methyl]-4-fluorodeprenyl and positron emission tomography studies in baboon brain.
Plenevaux, Alain mailto [Université de Liège - ULiège > > Centre de recherches du cyclotron >]
Dewey, Stephen L. [> > > >]
Fowler, Joanna S. [> > > >]
Guillaume, Marcel [> > > >]
Wolf, Alfred P. [ > > ]
Journal of Medicinal Chemistry
American Chemical Society
Yes (verified by ORBi)
[en] Animals ; Brain/metabolism/radionuclide imaging ; Carbon Radioisotopes ; Corpus Striatum/metabolism/radionuclide imaging ; Isotope Labeling/methods ; Kinetics ; Phenethylamines/chemical synthesis ; Stereoisomerism ; Structure-Activity Relationship ; Tomography, Emission-Computed
[en] (R)-(-)- and (S)-(+)-alpha-methyl-beta-4-(fluorophenyl)-N-methyl-N- propynylethylamine [R)-(-)- and (S)-(+)-4-fluorodeprenyl) were synthesized via the reaction of 4-fluorobenzaldehyde with nitroethane followed by reduction with lithium aluminum hydride to produce racemic 4-fluoroamphetamine, which was resolved by recrystallization with L- or D-N-acetylleucine to yield (R)-(-)-4-fluoroamphetamine or (S)-(+)-4-fluoroamphetamine in greater than 96% enantiomeric excesses and in yields of 42 and 39%, respectively. Alkylation with propargyl bromide gave (R)-(-)- or (S)-(+)-4-fluoronordeprenyl which was reductively methylated (Borch conditions) to produce (R)-(-)- or (S)-(+)-4-fluorodeprenyl. Alkylation of (R)-(-)- or (S)-(+)-4-fluoronordeprenyl with carbon-11 labeled methyl iodide gave (R)-(-)- or (S)-(+)-[N-11C-methyl]-4-fluorodeprenyl in a radiochemical yield of 30-40%. Comparative PET studies of the two labeled enantiomers in baboons showed a significantly lower retention of radioactivity in the striatum for the (S)-(+) enantiomer relative to the (R)-(-) enantiomer.
Centre de Recherches du Cyclotron - CRC ; Brookhaven National Laboratory NY USA
Fonds de la Recherche Scientifique (Communauté française de Belgique) - F.R.S.-FNRS
Researchers ; Professionals ; Students

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