Synthesis of 3beta-(4-[18F]fluoromethylphenyl)- and 3beta-(2-[18F] fluoromethylphenyl)tropane-2beta-carboxylic acid methyl esters: new ligands for mapping brain dopamine transporter with positron emission tomography.
The synthesis of two new dopamine transporter ligands, 3beta-(4-fluoromethylphenyl)tropane-2beta-carboxylic acid methyl ester and 3beta-(2-fluoromethylphenyl)tropane-2beta-carboxylic acid methyl ester, and their spectral characterization are described. The precursors for these ligands were prepared by TiCl4 catalyzed chloromethylation of 3beta-phenyltropane-2beta-carboxylic acid methyl ester followed by separation of the isomeric product mixture of 2- and 4-chloromethylphenyltropane derivatives. Reaction of the chloromethyl analogs with no-carrier-added [18F]fluoride ion followed by high performance liquid chromatography purification provided the corresponding [18F]fluoromethyltropanes, in good radiochemical yields, useful for imaging the brain dopamine transporter system in vivo with positron emission tomography.
Petric
A
A
Department of Molecular and Medical Pharmacology, UCLA School of Medicine, Los Angeles, California 90095-6948, USA. p6
Barrio
J R
JR
Namavari
M
M
Huang
S C
SC
Satyamurthy
N
N
D001921:Brain / Q000000981:diagnostic imaging / Q000378:metabolism*; D002352:Carrier Proteins / Q000032:analysis / Q000378:metabolism*; D003042:Cocaine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000493:pharmacokinetics; D004298:Dopamine / Q000378:metabolism; D050483:Dopamine Plasma Membrane Transport Proteins; D005462:Fluorine Radioisotopes / Q000493:pharmacokinetics*; D006801:Humans; D008562:Membrane Glycoproteins; D026901:Membrane Transport Proteins; D008968:Molecular Conformation; D015394:Molecular Structure; D009419:Nerve Tissue Proteins; D014055:Tomography, Emission-Computed / Q000379:methods
C400122:3beta-(2-fluoromethylphenyl)tropane-2beta-carboxylic acid methyl ester; C400123:3beta-(4-fluoromethylphenyl)tropane-2beta-carboxylic acid methyl ester; D002352:Carrier Proteins; D050483:Dopamine Plasma Membrane Transport Proteins; D005462:Fluorine Radioisotopes; D008562:Membrane Glycoproteins; D026901:Membrane Transport Proteins; D009419:Nerve Tissue Proteins; D003042:Cocaine; D004298:Dopamine