1. Intramolecular Friedel-Crafts Acylation of [ 11 C]Isocyanates Enabling the Radiolabeling of [carbonyl- 11 C]DPQ.
- Author
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Ozenil M, Kogler L, Mair BA, Hacker M, Wadsak W, Rotstein BH, and Pichler V
- Subjects
- Acylation, Isotope Labeling methods, Lactams chemistry, Carbon Radioisotopes chemistry, Radiopharmaceuticals chemistry, Radiopharmaceuticals chemical synthesis, Isocyanates chemistry, Positron-Emission Tomography methods
- Abstract
α,β-aromatic lactams are highly abundant in biologically active molecules, yet so far they cannot be radiolabeled with short-lived (t
1/2 =20.3 min), β+ -decaying carbon-11, which has prevented their application as positron emission tomography tracers. Herein, we developed, optimized, and applied a widely applicable, one-pot, quick, robust and automatable radiolabeling method for α,β-aromatic lactams starting from [11 C]CO2 using the reagent POCl3 ⋅AlCl3 . This method proceeds via intramolecular Friedel-Crafts acylation of in situ formed [11 C]isocyanates and shows a broad substrate scope for the formation of five- and six-membered rings. We implemented our developed labeling method for the radiosynthesis of the potential PARP1 PET tracer [carbonyl-11 C]DPQ in a clinical radiotracer production facility following the standards of the European Pharmacopoeia., (© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)- Published
- 2024
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