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【结 构 式】 
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【药物名称】 【化学名称】3-(2-Chlorophenyl)-1-(2,5-dihydroxyphenyl)-2-propen-1-one 【CA登记号】 【 分 子 式 】C15H11ClO3 【 分 子 量 】274.70612 |
【开发单位】Chungnam National University (Originator), Korea Res. Inst. Biosci. Biotechnol. (Originator) 【药理作用】Oncolytic Drugs, Angiogenesis Inhibitors |
合成路线1
Reaction of 2',5'-dihydroxyacetophenone (I) with dihydropyran (II) and pyridinium p-toluenesulfonate gives the protected bis-tetrahydropyranyl ether (III), which is submitted to Claisen-Schmidt condensation with 2-chlorobenzaldehyde (IV) in the presence of barium hydroxide, yielding the chalcone (V). Finally, the tetrahydropyranyl protecting groups of (V) are removed by acidic hydrolysis with p-toluenesulfonic acid in MeOH.
| 【1】 Nam, N.-H.; Kim, Y.; You, Y.-J.; Hong, D.-H.; Kim, H.-M.; Ahn, B.-Z.; Cytotoxic 2',5'-dihydroxychalcones with unexpected antiangiogenic activity. Eur J Med Chem 2003, 38, 2, 179. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 38479 | 1-(2,5-dihydroxyphenyl)-1-ethanone | 490-78-8 | C8H8O3 | 详情 | 详情 |
| (II) | 13684 | 3,4-Dihydro-2H-pyran;2,3-Dihydro-4H-pyran; 5,6-Dihydro-4H-pyran;Dihydropyran | 110-87-2 | C5H8O | 详情 | 详情 |
| (III) | 64828 | 1-[2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]-1-ethanone | C18H24O5 | 详情 | 详情 | |
| (IV) | 24114 | 2-chlorobenzaldehyde | 89-98-5 | C7H5ClO | 详情 | 详情 |
| (V) | 64829 | (E)-1-[2,5-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]-3-(2-chlorophenyl)-2-propen-1-one | C25H27ClO5 | 详情 | 详情 |
Extended Information