Synthesis of [F-18]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide], a marker for PET detection of hypoxia

Josse, Olivier;Grégoire, Vincent;Labar, Daniel;Georges, Benoît;Marchand-Brynaert, Jacqueline
(2001) Bioorganic & Medicinal Chemistry : the tetrahedron journal for research at the interface of chemistry and biology — Vol. 9, n° 3, p. 665-675 (2001)

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Authors
  • Josse, OlivierUCLouvain
    Author
  • Grégoire, VincentUCLouvain
    Author
  • Labar, DanielUCLouvain
    Author
  • Georges, BenoîtUCLouvain
    Author
  • Marchand-Brynaert, JacquelineUCLouvain
    Author
Abstract
[F-18]-2-(2-Nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide ([F-18]-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 [F-18]-3,3,3-trifluoropropylamine 7. This original radiolabelled key-synthon was obtained in 40% overall chemical yield by oxidative [F-18]-fluorodesulfurization of ethyl N-phthalimido-3-aminopropane dithioate 4, followed by deprotection with hydrazine of the resulting [F-18]-N-phthalimido-3,3,3-trifluoropropylamine 5. All the process was performed within 90 min, from the [F-18]-HF production in the cyclotron to the purification of the final target. (C) 2001 Elsevier Science Ltd. All rights reserved.
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Josse, O., Grégoire, V., Labar, D., Georges, B., & Marchand-Brynaert, J. (2001). Synthesis of [F-18]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide], a marker for PET detection of hypoxia. Bioorganic & Medicinal Chemistry : the tetrahedron journal for research at the interface of chemistry and biology, 9(3), 665-675. https://doi.org/10.1016/S0968-0896(00)00279-0 (Original work published 2001)