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 |
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Authors: | Ando Yuko Ando Kumiko Yamaguchi Mami Kunitomo Jun-ichi Koida Masao Fukuyama Ryo Nakamuta Hiromichi Yamashita Masayuki Ohta Shunsaku Ohishi Yoshitaka |
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Institution: | Department of Medicinal and Synthetic Chemistry, Faculty of Pharmaceutical Sciences, Mukogawa Women's University, Nishinomiya 663-8179, Japan. |
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Abstract: | A novel oxazine ring formation method was established using the reaction of 2-acetyl-(E)-3-styrylcarbonylaminobenzob]furans (4) with Vilsmeier-Haack-Arnold reagent to afford (E and Z)-((E)-2-styrylbenzob]furo3,2-d]1,3]oxazin-4-ylideno)acetaldehydes (5). (Z)-4-(8-Bromo-(E)-2-styrylbenzob]furo3,2-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). |
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