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【结 构 式】 
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【药物名称】 【化学名称】(6R,8aS)-6-Hydroxy-3-methoxy-11-(8-phthalimidooctyl)-5,6,9,10-tetrahydro-4aH-benzofuro[3a,3,2-ef][2]benzazepinium bromide 【CA登记号】 【 分 子 式 】C32H37BrN2O5 【 分 子 量 】609.56609 |
【开发单位】SCRAS (Originator) 【药理作用】Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, Acetylcholinesterase Inhibitors |
合成路线1
Alkylation of potassium phthalimide (I) with an excess of 1,8-dibromooctane (II) in refluxing acetone afforded N-(8-bromooctyl)phthalimide (III). This was condensed with 6-O-demethylgalanthamine (IV) in the presence of Et3N in boiling acetonitrile to give phthalimidooctyl compound (V). Finally, reaction with N-bromosuccinimide in the presence of azobisisobutyronitrile provided the iminium bromide.
| 【1】 Mary, A.; Renko, D.Z.; Guillou, C.; Thal, C.; Potent acetylcholinesterase inhibitors: Design, synthesis, and structure-activity relationships of bis-interacting ligands in the galanthamine series. Bioorg Med Chem 1998, 6, 10, 1835. |
| 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) | 10926 | (1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)potassium | C8H4KNO2 | 详情 | 详情 | |
| (II) | 18610 | 1,8-dibromooctane | 4549-32-0 | C8H16Br2 | 详情 | 详情 |
| (III) | 18611 | 2-(8-bromooctyl)-1H-isoindole-1,3(2H)-dione | 17702-83-9 | C16H20BrNO2 | 详情 | 详情 |
| (IV) | 18612 | (6R,8aS)-3-methoxy-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol | C16H19NO3 | 详情 | 详情 | |
| (V) | 18613 | 2-[8-[(6R,8aS)-6-hydroxy-3-methoxy-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11(12H)-yl]octyl]-1H-isoindole-1,3(2H)-dione | C32H38N2O5 | 详情 | 详情 |
Extended Information