The synthesis and characterization of BMS-204352 (MaxiPost™) and related 3-fluorooxindoles as openers of maxi-K potassium channels

3-Aryl-3-fluorooxindoles can be efficiently synthesized in two steps by the addition of an aryl Grignard to an isatin, followed by treatment with DAST. Oxindole 1 (BMS-204352; MaxiPost(TM)) can be isolated using chiral HPLC or prepared by employing chiral resolution. Cloned maxi-K channels are opened by 1, which demonstrates a brain/plasma ratio > 9 in rats. (C) 2002 Elsevier Science Ltd, All rights reserved.