Synthesis of N-(2,5-dimethoxybenzyl)-N-(5-fluoro-2-phenoxyphenyl)[carbonyl-11C]aceta mide ([carbonyl-11C]DAA1106) and analogues using [11C]carbon monoxide and palladium(0) complex
2007 (English)In: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 50, no 13, 1192-1199 p.Article in journal (Refereed) Published
N-(2,5-Dimethoxybenzyl)-N-(5-fluoro-2-phenoxyphenyl)acetamide (DAA1106), a potent and selective ligand for peripheral benzodiazepine receptor, and eight structurally related analogues were labelled with 11C at the carbonyl position using a low concentration of [11C]carbon monoxide and the micro-autoclave technique. A combinatorial approach was applied to synthesize the analogues using similar reaction conditions. Palladium-mediated carbonylation using tetrakis(triphenylphosphine)palladium, various amines and methyl iodide or iodobenzene was employed in the synthesis. The 11C-labelled products were obtained with 10-55% decay-corrected radiochemical yields and the final product was more than 97% pure in all cases. Specific radioactivity was determined for the compound [carbonyl-11C]DAA1106 using a single experiment and a 10-μAh bombardment. The specific radioactivity, measured 36min after end of bombardment, was 455 GBq/μmol. Synthetic routes to the precursors and reference compounds were also developed. The presented approach is a novel method for the synthesis of [carbonyl-11C]DAA1106 and its analogues, and allows the formation of a library of 11C-labelled DAA1106 analogues which can be used to optimize the performance as a potential positron emission tomography tracer.
Place, publisher, year, edition, pages
2007. Vol. 50, no 13, 1192-1199 p.
[11C]carbon monoxide, [11C]DAA1106, palladium(0), micro-autoclave
IdentifiersURN: urn:nbn:se:uu:diva-14974DOI: 10.1002/jlcr.1437ISI: 000253063800009OAI: oai:DiVA.org:uu-14974DiVA: diva2:42745