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Synthesis, attempted kinetic resolution and evaluation of [ 123 I]‐MK‐447 analogues as inflammation radiopharmaceuticals
Author(s) -
Siu Anna F. M.,
Lambrecht Richard M.,
Shani Jashovam,
Pyne Stephen G.,
KaneMaguire Leon A. P.
Publication year - 1997
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/(sici)1099-1344(199709)39:9<711::aid-jlcr22>3.0.co;2-a
Subject(s) - chemistry , diastereomer , hydrochloride , inflammation , kinetic resolution , stereochemistry , enantioselective synthesis , biochemistry , catalysis , medicine
The non‐steroidal anti‐inflammatory agent 2‐amino‐methyl‐4‐tert‐butyl‐6‐iodophenol hydrochloride (MK‐447) and some of its analogues were labelled with 123 I and tested in an inflamed rat‐paw model. Even though MK‐447 has a significant anti‐inflammatory activity, and a 2.3 ratio for inflamed site over muscle, its usefulness for scintigraphic detection of inflammation is hindered by its high uptake in the skin. The kinetic resolution of diastereomeric products with chiral dienyl iron complexes was unsuccessful as the signals from the respective 1 H and 13 C NMR spectra were coincident. © 1997 John Wiley & Sons, Ltd.