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
| Autor: | Kumiko Ando, Shunsaku Ohta, Masao Koida, Yoshitaka Ohishi, Jun-ichi Kunitomo, Mami Yamaguchi, Masayuki Yamashita, Yuko Ando, Hiromichi Nakamuta, Ryo Fukuyama |
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| Rok vydání: | 2006 |
| Předmět: |
Stereochemistry
Clinical Biochemistry Closure (topology) Osteoclasts Pharmaceutical Science Ring (chemistry) Biochemistry Chemical synthesis Bone resorption D-1 Oxazines Drug Discovery Humans Bone Resorption Molecular Biology Benzofurans Estradiol Chemistry Organic Chemistry General Medicine Ethyl ester Resorption Models Chemical Reagent Molecular Medicine Female |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 16:5849-5854 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/j.bmcl.2006.08.064 |
| Popis: | 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 17 β -estradiol (E 2 ). |
| Databáze: | OpenAIRE |
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