11 C-Labeling of Aryl Ketones as Candidate Histamine Subtype-3 Receptor PET Radioligands through Pd(0)-Mediated 11 C-Carbonylative Coupling

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Fabrice G SiméonVictor W Pike

Abstract

Pd(0)-mediated coupling between iodoarenes, [11C]carbon monoxide and aryltributylstannanes has been used to prepare simple model [11C]aryl ketones. Here, we aimed to label four 2-aminoethylbenzofuran chemotype based molecules ([11C]1-4) in the carbonyl position, as prospective positron emission tomography (PET) radioligands for the histamine subtype 3 receptor (H3R) by adapting this methodology with use of aryltrimethylstannanes. Radiosynthesis was successfully performed on a platform equipped with a mini-autoclave and a liquid handling robotic arm, within a lead-shielded hot-cell. Candidate radioligands were readily formulated in saline containing ethanol (10%, v/v) and ascorbic acid (0.5 mg/10 mL). Yields for preclinical use were in the range of 5-9%, decay-corrected from cyclotron-produced [11C]CO₂ and molar activities were >115 GBq/µmol at end of synthesis. Radiochemical purities exceeded >97%.

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Citations

Jan 18, 2018·Expert Opinion on Therapeutic Patents·Dorota Łażewska, Katarzyna Kieć-Kononowicz
Oct 30, 2019·EJNMMI Radiopharmacy and Chemistry·Carlotta Taddei, Victor W Pike

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