Syntheses of the phosphodiesterase-4 inhibitors [11C]Ro 20-1724, R-, R/S- and S-[11C]rolipram

The high affinity and selective cAMP‐specific phosphodiesterase‐4 inhibitors Ro 20‐1724, R‐, R/S‐ and S‐rolipram were labeled with 11C by O‐[11C]methylation of their respective phenolic precursors using [11C]methyl iodide. The desmethyl precursor of Ro 20‐1724 was prepared by selective dealkylation...

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Bibliographic Details
Published in:Journal of labelled compounds & radiopharmaceuticals 2001-04, Vol.44 (5), p.373-384
Main Authors: DaSilva, Jean N., Lourenco, Celia M., Wilson, Alan A., Houle, Sylvain
Format: Article
Language:English
Subjects:
Biological and medical sciences
cAMP
carbon-11
Contrast media. Radiopharmaceuticals
enzyme
Medical sciences
O-[11C]methylation
PDE4
Pharmacology. Drug treatments
positron emission tomography
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Summary:The high affinity and selective cAMP‐specific phosphodiesterase‐4 inhibitors Ro 20‐1724, R‐, R/S‐ and S‐rolipram were labeled with 11C by O‐[11C]methylation of their respective phenolic precursors using [11C]methyl iodide. The desmethyl precursor of Ro 20‐1724 was prepared by selective dealkylation with iodotrimethylsilane, whereas, dealkylation of racemic rolipram was not selective and yielded several products. Enantiomeric separation of R‐ and S‐desmethylrolipram was carried out by chiral semi‐preparative high performance liquid chromatography. The final 11C‐labeled products were prepared in high radiochemical purity (>99%), yields (45‐75%, decay‐corrected) and specific activities [18.5‐92.5 GBq/µmol], within 30 min from end‐of‐bombardment. Copyright © 2001 John Wiley & Sons, Ltd.
ISSN:0362-4803
1099-1344
DOI:10.1002/jlcr.465