Synthesis, attempted kinetic resolution and evaluation of [123I]-MK-447 analogues as inflammation radiopharmaceuticals

Article abstract of DOI:10.1002/(SICI)1099-1344(199709)39:9<711::AID-JLCR22>3.0.CO;2-A

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 ¹²³I 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 usefullness 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 ¹H and ¹³C NMR spectra were coincident.