title: A novel oxazine ring closure reaction affording (Z)-((E)-2-styrylbenzo[b]furo[3,2-d][1,3]oxazin-4-ylideno)acetaldehydes and their anti-osteoclastic bone resorption activity.
abstract: A novel oxazine ring formation method was established using the reaction of 2-acetyl-(E)-3-styrylcarbonylaminobenzo[b]furans (4) with Vilsmeier-Haack-Arnold reagent to afford (E and Z)-((E)-2-styrylbenzo[b]furo[3,2-d][1,3]oxazin-4-ylideno)acetaldehydes (5). (Z)-4-(8-Bromo-(E)-2-styrylbenzo[b]furo[3,2-d][1,3]oxazin-4-ylideno)but-(E)-2-enoic acid ethyl ester (6b), derived from (Z)-5a, showed significantly potent anti-osteoclastic bone resorption activity comparable to 17beta-estradiol (E2).
authors.affiliation: Department of Medicinal and Synthetic Chemistry, Faculty of Pharmaceutical Sciences, Mukogawa Women's University, Nishinomiya 663-8179, Japan.
authors.forename: Yuko
authors.initials: Y
authors.lastname: Ando
authors.forename: Kumiko
authors.initials: K
authors.lastname: Ando
authors.forename: Mami
authors.initials: M
authors.lastname: Yamaguchi
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Kunitomo
authors.forename: Masao
authors.initials: M
authors.lastname: Koida
authors.forename: Ryo
authors.initials: R
authors.lastname: Fukuyama
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Nakamuta
authors.forename: Masayuki
authors.initials: M
authors.lastname: Yamashita
authors.forename: Shunsaku
authors.initials: S
authors.lastname: Ohta
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Ohishi
mesh_terms: D001572:Benzofurans / Q000737:chemistry* / Q000494:pharmacology*; D001862:Bone Resorption / Q000188:drug therapy*; D004958:Estradiol / Q000494:pharmacology; D005260:Female; D006801:Humans; D008956:Models, Chemical; D010010:Osteoclasts / Q000166:cytology / Q000187:drug effects*; D010078:Oxazines / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D001572:Benzofurans; D010078:Oxazines; D004958:Estradiol