Perfluorinated markers for hypoxia detection: synthesis of sulfur-containing precursors and [18F]-labelling.

Cheguillaume, Arnaud;Gillart, Jacques;Labar, Daniel;Grégoire, Vincent;Marchand-Brynaert, Jacqueline
(2005) Bioorganic & Medicinal Chemistry : the tetrahedron journal for research at the interface of chemistry and biology — Vol. 13, n° 4, p. 1357-1367 (2005)

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Authors
  • Cheguillaume, Arnaud
    Author
  • Gillart, JacquesUCLouvain
    Author
  • Labar, DanielUCLouvain
    Author
  • Grégoire, VincentUCLouvain
    Author
  • Marchand-Brynaert, JacquelineUCLouvain
    Author
Abstract
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.
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Cheguillaume, A., Gillart, J., Labar, D., Grégoire, V., & Marchand-Brynaert, J. (2005). Perfluorinated markers for hypoxia detection: synthesis of sulfur-containing precursors and [18F]-labelling. Bioorganic & Medicinal Chemistry : the tetrahedron journal for research at the interface of chemistry and biology, 13(4), 1357-1367. https://doi.org/10.1016/j.bmc.2004.11.010 (Original work published 2005)