Intramolecular Friedel-Crafts Acylation of [11C]Isocyanates Enabling the Radiolabeling of [carbonyl-11C]DPQ.
Chemistry
; 30(28): e202400581, 2024 May 17.
Article
em En
| MEDLINE
| ID: mdl-38470445
ABSTRACT
α,ß-aromatic lactams are highly abundant in biologically active molecules, yet so far they cannot be radiolabeled with short-lived (t1/2=20.3â
min), ß+-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,ß-aromatic lactams starting from [11C]CO2 using the reagent POCl3â
AlCl3. This method proceeds via intramolecular Friedel-Crafts acylation of inâ
situ formed [11C]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-11C]DPQ in a clinical radiotracer production facility following the standards of the European Pharmacopoeia.
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01-internacional
Base de dados:
MEDLINE
Assunto principal:
Radioisótopos de Carbono
/
Isocianatos
/
Compostos Radiofarmacêuticos
/
Tomografia por Emissão de Pósitrons
Idioma:
En
Ano de publicação:
2024
Tipo de documento:
Article