title: Synthesis and biological activities of optically active 6-[3-(3,4-dimethoxybenzylamino)-2-hydroxypropoxy]-2(1H)-quinolinone (OPC-18790).
abstract: The enantiomers of 6-[3-(3,4-dimethoxybenzylamino)-2-hydroxypropoxy]-2(1H)-quinolinon e (OPC-18790), a novel cardiotonic agent, were synthesized and evaluated for positive inotropic activity. The key intermediates, 2,3-epoxypropoxy derivatives, were obtained by the alkylation of 6-hydroxy-2(1H)-quinolinone with optically active epichlorohydrin and subsequent ring closure. In an in vitro study, the (R)-(+)-isomer was about 10-fold more potent than the (S)-(-)-isomer.
authors.affiliation: 2nd Tokushima Institute of New Drug Research, Otsuka Pharmaceutical Co., Ltd., Japan.
authors.forename: T
authors.initials: T
authors.lastname: Fujioka
authors.forename: S
authors.initials: S
authors.lastname: Teramoto
authors.forename: S
authors.initials: S
authors.lastname: Tsujimi
authors.forename: K
authors.initials: K
authors.lastname: Takemoto
authors.forename: T
authors.initials: T
authors.lastname: Mori
authors.forename: T
authors.initials: T
authors.lastname: Hosokawa
authors.forename: T
authors.initials: T
authors.lastname: Sumida
authors.forename: M
authors.initials: M
authors.lastname: Tominaga
authors.forename: Y
authors.initials: Y
authors.lastname: Yabuuchi
mesh_terms: D000818:Animals; D002316:Cardiotonic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D004285:Dogs; D066298:In Vitro Techniques; D009200:Myocardial Contraction / Q000187:drug effects; D015363:Quinolones / Q000138:chemical synthesis* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D002316:Cardiotonic Agents; D015363:Quinolones; C077543:toborinone