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.
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).
Ando
Yuko
Y
Department of Medicinal and Synthetic Chemistry, Faculty of Pharmaceutical Sciences, Mukogawa Women's University, Nishinomiya 663-8179, Japan.
Ando
Kumiko
K
Yamaguchi
Mami
M
Kunitomo
Jun-ichi
J
Koida
Masao
M
Fukuyama
Ryo
R
Nakamuta
Hiromichi
H
Yamashita
Masayuki
M
Ohta
Shunsaku
S
Ohishi
Yoshitaka
Y
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*
D001572:Benzofurans; D010078:Oxazines; D004958:Estradiol