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【结 构 式】 
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【药物名称】DA-6034 【化学名称】2-[2-(3,4-Dimethoxyphenyl)-5-methoxy-4-oxo-4H-1-benzopyran-7-yloxy]acetic acid 【CA登记号】203191-10-0 【 分 子 式 】C20H18O8 【 分 子 量 】386.36166 |
【开发单位】Dong-A (Originator) 【药理作用】GASTROINTESTINAL DRUGS, Inflammatory Bowel Disease, Agents for, Leukotriene Synthesis Inhibitors |
合成路线1
The condensation of 4-benzyloxy-2-hydroxy-6-methoxyacetophenone (I) with 3,4-dimethoxybenzaldehyde (II) by means of KOH in ethanol/water gives the chalcone (III), which is cyclized by means of SeO2 in refluxing isoamyl alcohol to yield the benzopyran (IV). The hydrogenolysis of the benzyl group of (IV) with H2 over Pd/C in chloroform affords the 7-hydroxybenzopyran (V), which is condensed with tert-butyl bromoacetate (VII) by means of CaCO3 in DMF to provide the benzopyranyloxy acetate (VIII). Finally, this compound is deprotected by reaction with p-toluenesulfonic acid in refluxing benzene.
| 【1】 Yoo, M.; Son, M.W.; Kin, I.Y.; Kin, W.B.; Kin, S.H.; Lee, S.D.; Lim, G.J.; Lim, J.I.; Ahn, B.O.; Baik, N.G.; Kin, D.S.; Oh, T.Y.; Ryu, B.K.; Yang, J.S.; Shin, H.C. (Dong-A Pharmaceutical Co., Ltd.); Gastroprotective flavone/flavone cpds. with therapeutic effect on inflammatory bowel disease. JP 1999514015; US 6025387; WO 9804541 . |
| 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) | 27802 | 1-[4-(benzyloxy)-2-hydroxy-6-methoxyphenyl]-1-ethanone | C16H16O4 | 详情 | 详情 | |
| (II) | 18304 | 3,4-Dimethoxybenzaldehyde; Veratraldehyde | 120-14-9 | C9H10O3 | 详情 | 详情 |
| (III) | 27803 | (E)-1-[4-(benzyloxy)-2-hydroxy-6-methoxyphenyl]-3-(3,4-dimethoxyphenyl)-2-propen-1-one | C25H24O6 | 详情 | 详情 | |
| (IV) | 27804 | 7-(benzyloxy)-2-(3,4-dimethoxyphenyl)-5-methoxy-4H-chromen-4-one | C25H22O6 | 详情 | 详情 | |
| (V) | 27805 | 2-(3,4-dimethoxyphenyl)-7-hydroxy-5-methoxy-4H-chromen-4-one | C18H16O6 | 详情 | 详情 | |
| (VI) | 17430 | 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate | 5292-43-3 | C6H11BrO2 | 详情 | 详情 |
| (VII) | 27806 | tert-butyl 2-[[2-(3,4-dimethoxyphenyl)-5-methoxy-4-oxo-4H-chromen-7-yl]oxy]acetate | C24H26O8 | 详情 | 详情 |