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Synthesis and evaluation of [ 123 I]‐indomethacin derivatives as COX‐2 targeted imaging agents
Author(s) -
Uddin Md. Jashim,
Crews Brenda C.,
Blobaum Anna L.,
Kingsley Philip J.,
Ghebreselasie Kebreab,
Saleh Sam S.,
Clanton Jeffrey A.,
Baldwin Ronald M.,
Marnett Lawrence J.
Publication year - 2009
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1615
Subject(s) - chemistry , yield (engineering) , acetamide , triphenylphosphine , nuclear chemistry , chloramine t , palladium , in vivo , medicinal chemistry , organic chemistry , catalysis , materials science , microbiology and biotechnology , metallurgy , biology
A novel series of iodinated indomethacin derivatives was synthesized, and evaluated as selective inhibitors of COX‐2. Two candidate compounds N ‐( p ‐iodobenzyl)‐2‐(1‐( p ‐chlorobenzoyl)‐5‐methoxy‐2‐methyl‐1 H ‐indol‐3‐yl)acetamide (3) and 1‐( p ‐iodobenzyl)‐5‐methoxy‐2‐methyl‐3‐indoleacetic acid (9) possessed optimum properties suitable for potential in vivo imaging. Arylstannane precursors for radioiododestannylation were synthesized in 70–85% yield from the iodo compounds by reaction with hexabutylditin and tetrakis (triphenylphosphine)palladium(0) in refluxing dioxane. Radioiododestannylation was conducted by reaction with carrier‐added Na[ 123 I] in the presence of Chloramine‐T in an EtOAc/H 2 O binary system under acidic conditions (pH 3.5), allowing direct isolation of the labeled products by separation of the organic phase. Radioiodinated products [ 123 I]3 and [ 123 I]9 were recovered in a decay‐corrected radiochemical yield of 86–87% and radiochemical purity of 98–99%. Copyright © 2009 John Wiley & Sons, Ltd.