Perfluorinated markers for hypoxia detection: synthesis of sulfur-containing precursors and [18F]-labelling.
Synthetic pathways of two novel sulfurated precursors for [18F]-labelling by oxidative fluorodesulfurization reaction are described. A three-step sequence starting from N-phthalimido-beta-alanine allows the preparation of a new trithioorthoester as valuable precursor of the synthesis of [18F]-3,3,3-trifluoropropylamine, a convenient radiolabelled intermediate for [18F]-EF3. A five-step sequence for the preparation of methyl 4-phthalimido-2,2-difluoropropanedithioate from ethyl 2,2-difluoropropanoate, via the key conversion step of alpha,alpha'-difluorothioamidate to the corresponding alpha,alpha'-difluorodithioester, and the first results of its use as precursor for oxidative fluorodesulfurization in [18F]-radiochemistry are also presented.
Cheguillaume
Arnaud
A
Unité de Chimie Organique et Médicinale, Bâtiment Lavoisier, place L. Pasteur, Université catholique de Louvain, B-1348 Louvain-la-Neuve, Belgium.
Gillart
Jacques
J
Labar
Daniel
D
Grégoire
Vincent
V
Marchand-Brynaert
Jacqueline
J
D005462:Fluorine Radioisotopes / Q000737:chemistry*; D000860:Hypoxia / Q000175:diagnosis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013455:Sulfur / Q000737:chemistry*
D005462:Fluorine Radioisotopes; D013455:Sulfur