title: The synthesis and characterization of BMS-204352 (MaxiPost) and related 3-fluorooxindoles as openers of maxi-K potassium channels.
abstract: 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) 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.
authors.affiliation: Department of Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, CT 06492, USA.
authors.forename: Piyasena
authors.initials: P
authors.lastname: Hewawasam
authors.forename: Valentin K
authors.initials: VK
authors.lastname: Gribkoff
authors.forename: Yadagiri
authors.initials: Y
authors.lastname: Pendri
authors.forename: Steven I
authors.initials: SI
authors.lastname: Dworetzky
authors.forename: Nicholas A
authors.initials: NA
authors.lastname: Meanwell
authors.forename: Eduardo
authors.initials: E
authors.lastname: Martinez
authors.forename: Christopher G
authors.initials: CG
authors.lastname: Boissard
authors.forename: Debra J
authors.initials: DJ
authors.lastname: Post-Munson
authors.forename: Joanne T
authors.initials: JT
authors.lastname: Trojnacki
authors.forename: Krishnaswamy
authors.initials: K
authors.lastname: Yeleswaram
authors.forename: Lorraine M
authors.initials: LM
authors.lastname: Pajor
authors.forename: Jay
authors.initials: J
authors.lastname: Knipe
authors.forename: Qi
authors.initials: Q
authors.lastname: Gao
authors.forename: Robert
authors.initials: R
authors.lastname: Perrone
authors.forename: John E
authors.initials: JE
authors.lastname: Starrett
mesh_terms: D000818:Animals; D001921:Brain / Q000187:drug effects* / Q000378:metabolism; D002118:Calcium / Q000378:metabolism; D002478:Cells, Cultured / Q000187:drug effects; D003979:Diazonium Compounds; D006801:Humans; D007211:Indoles / Q000097:blood / Q000138:chemical synthesis* / Q000494:pharmacology*; D051036:Large-Conductance Calcium-Activated Potassium Channels; D008297:Male; D008845:Microinjections; D009865:Oocytes / Q000187:drug effects* / Q000502:physiology*; D018408:Patch-Clamp Techniques; D024681:Potassium Channels, Calcium-Activated / Q000187:drug effects* / Q000235:genetics / Q000378:metabolism; D012333:RNA, Messenger / Q000378:metabolism; D051381:Rats; D017207:Rats, Sprague-Dawley; D014981:Xenopus
chemical_list: C424388:BMS204352; D003979:Diazonium Compounds; D007211:Indoles; D051036:Large-Conductance Calcium-Activated Potassium Channels; D024681:Potassium Channels, Calcium-Activated; D012333:RNA, Messenger; C408750:selectfluor; D002118:Calcium