ORBi: Plenevaux Alain - Synthesis of (R)-(-)- and (S)-(+)-4-fluorodeprenyl and (R)-(-)- and (S)-(+)-[N-11C-methyl]-4-fluorodeprenyl and positron emission tomography studies in baboon brain.

Reference : Synthesis of (R)-(-)- and (S)-(+)-4-fluorodeprenyl and (R)-(-)- and (S)-(+)-[N-11C-methy...


	Document type :	Scientific journals : Article
	Discipline(s) :	Human health sciences : Radiology, nuclear medicine & imaging
	To cite this reference:	http://hdl.handle.net/2268/5270

Title :	Synthesis of (R)-(-)- and (S)-(+)-4-fluorodeprenyl and (R)-(-)- and (S)-(+)-[N-11C-methyl]-4-fluorodeprenyl and positron emission tomography studies in baboon brain.
Language :	English
Author, co-author :	Plenevaux, Alain [Université de Liège - ULg > > Centre de recherches du cyclotron >]
	Dewey, Stephen L. [> > > >]
	Fowler, Joanna S. [> > > >]
	Guillaume, Marcel [> > > >]
	Wolf, Alfred P. [ > > ]
Publication date :	1990
Journal title :	Journal of Medicinal Chemistry
Publisher :	American Chemical Society
Volume :	33
Issue/season :	7
Pages :	2015-9
Peer reviewed :	Yes (verified by ORBi)
Audience :	International
ISSN :	0022-2623
e-ISSN :	1520-4804
City :	Washington
Country :	DC
Keywords :	[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
Abstract :	[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.
Research units :	Centre de Recherches du Cyclotron - CRC ; Brookhaven National Laboratory NY USA
Funders :	Fonds de la Recherche Scientifique (Communauté française de Belgique) - F.R.S.-FNRS
Target :	Researchers ; Professionals ; Students
Permalink :	http://hdl.handle.net/2268/5270

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	File	Commentary	Version	Size	Access
Restricted access	J Med Chem 1990_Plenevaux_11CFDeprenyl.pdf	No commentary	Publisher postprint	6.06 MB	Request copy

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