Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity |
| |
| Authors: | Yukako Tabuchi Yuko Ando Hidemi Kanemura Ikuo Kawasaki Takahiro Ohishi Masao Koida Ryo Fukuyama Hiromichi Nakamuta Shunsaku Ohta Kiyoharu Nishide Yoshitaka Ohishi |
| |
| Institution: | 1. School of Pharmaceutical Sciences, Mukogawa Women’s University, 11-68 Koshien Kyubancho, Nishinomiya, Hyogo 663-8179, Japan;2. Science of Environment and Mathematical Modeling, Graduate School of Engineering, Doshisha University, Kyotanabe, Kyoto 610-0394, Japan;3. Department of Pharmacology, Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata, Osaka 573-1010, Japan;4. Laboratory of Pharmacology, Department of Pharmaceutical Sciences, Faculty of Pharmaceutical Sciences, Hiroshima International University, 5-1-1 Hirokoshinkai, Kure, Hiroshima 737-0112, Japan;5. Kyoto Pharmaceutical University, Misasagi, Yamashinaku, Kyoto 607-8412, Japan;6. Taisho Pharm. Ind., Ltd, Research & Development Dept., 3, Oharaichiba, Koka-cho, Koka, Shiga 520-3433, Japan |
| |
| Abstract: | A reaction of 2-acetyl-3-acylaminobenzob]furans (9d–o) with Vilsmeier (VM) reagent afforded a mixture of (E)- and (Z)-{(E)-2-aralkenylbenzob]furo3,2-d]1,3]oxazin-4-ylidene}acetaldehydes (5) with a characteristic exo-formylmethylene group on the oxazine ring. The Z-isomer was more stable than the E-isomer. The Z-isomers ((Z)-5) were reacted with phosphonate reagents under two different conditions to obtain various butadiene derivatives (12) containing benzob]furo3,2-d]1,3]oxazine skeleton. Typical compounds (5 and 12) were evaluated for their anti-osteoclastic bone resorption activity, antagonistic activity for the cysLT1 receptor and growth inhibitory activity for MIA PaCa-2 and MCF-7. Compounds 12f and 12j showed potent anti-osteoclastic bone resorption activity comparable to E2 (17β-estradiol). |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
