Synthesis of [18F]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide], a marker for PET detection of hypoxia.
[18F]-2-(2-Nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide ([18F]-EF3) has been prepared, in 65% chemical yield and 5% radiochemical yield, by coupling 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl) acetate 1 with [18F]-3,3,3-trifluoropropylamine 7. This original radiolabelled key-synthon was obtained in 40% overall chemical yield by oxidative [18F]-fluorodesulfurization of ethyl N-phthalimido-3-aminopropane dithioate 4, followed by deprotection with hydrazine of the resulting [18F]-N-phthalimido-3,3,3-trifluoropropylamine 5. All the process was performed within 90 min, from the [18F]-HF production in the cyclotron to the purification of the final target.
Josse
O
O
Unité de Chimie Organique et Médicinale, Université catholique de Louvain, Louvain-la-Neuve, Belgium.
Labar
D
D
Georges
B
B
Grégoire
V
V
Marchand-Brynaert
J
J
D005462:Fluorine Radioisotopes; D006801:Humans; D000860:Hypoxia / Q000175:diagnosis / Q000000981:diagnostic imaging*; D009593:Nitroimidazoles / Q000138:chemical synthesis; D011829:Radiation Dosage; D019275:Radiopharmaceuticals / Q000138:chemical synthesis; D013329:Structure-Activity Relationship; D014055:Tomography, Emission-Computed
C438056:2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide; D005462:Fluorine Radioisotopes; D009593:Nitroimidazoles; D019275:Radiopharmaceuticals