title: Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity.
abstract: Novel 3-acetoacetylaminobenzo[b]furan derivatives having a modified triene system at the 3-position were synthesized starting with 3-aminobenzo[b]furans. The enol isomers, 3-[(3-hydroxybut-2-enonyl)amino]benzo[b]furans (), of the 3-acetoacetylaminobenzo[b]furans were obtained as stable isomers owing to formation of a hydrogen bonding between the enol hydroxyl group and the amidocarbonyl group. The planarity of the C-2 substituent through the C-3 side chain suggested the existence of a modified conjugational triene system in the enol compound. Cysteinyl leukotriene 1 and 2 receptor antagonistic activities for these compounds were evaluated. 2-(4-Cyanobenzoyl or ethoxycarbonyl)-3-[(2-cyano-3-hydroxybut-2-enonyl)amino]benzo[b]furans (, ) were moderately active.
authors.affiliation: School of Pharmaceutical Sciences, Mukogawa-Women's University, 11-68 Koshien Kyuban-cho, Nishinomiya 663-8179, Japan.
authors.forename: Kumiko
authors.initials: K
authors.lastname: Ando
authors.forename: Eriko
authors.initials: E
authors.lastname: Tsuji
authors.forename: Yuko
authors.initials: Y
authors.lastname: Ando
authors.forename: Noriko
authors.initials: N
authors.lastname: Kuwata
authors.forename: Jun-Ichi
authors.initials: J
authors.lastname: Kunitomo
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yamashita
authors.forename: Shunsaku
authors.initials: S
authors.lastname: Ohta
authors.forename: Shigekatsu
authors.initials: S
authors.lastname: Kohno
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Ohishi
mesh_terms: D000818:Animals; D001572:Benzofurans / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D006224:Cricetinae; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D018077:Receptors, Leukotriene / Q000378:metabolism*; D013329:Structure-Activity Relationship
chemical_list: D001572:Benzofurans; D018077:Receptors, Leukotriene; C412375:cysteinyl leukotriene receptor 2