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【结 构 式】 
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【药物名称】 【化学名称】1-Ethyl-3-[(4-fluorophenyl)(1H-imidazol-1-yl)methyl]-1H-indole 【CA登记号】 【 分 子 式 】C20H18FN3 【 分 子 量 】319.38496 |
【开发单位】Universität des Saarlandes (Originator) 【药理作用】ONCOLYTIC DRUGS, Aromatase Inhibitors |
合成路线1
The acylation of indole (I) with 4-fluorobenzoyl chloride (II) by means of AlCl3 in dichloromethane gives 3-(4-fluorobenzoyl)indole (III), which is N-alkylated with ethyl iodide and K2CO3 in acetone yielding 1-ethyl-3-(4-fluorobenzoyl)indole (IV). The reduction of (IV) with NaBH4 in methanol affords the corresponding carbinol (V), which is finally treated with carbonyl diimidazole (VI) in THF.
| 【1】 Marchand, P.; Robert, J.-M.; Palzer, M.; Delovoye-Seiller, B.; Hartmann, R.W.; Le Baut, G.; Le Borgne, M.; New selective nonsteroidal aromatase inhibitors: Synthesis and inhibitory activity of 2, 3 or 5-(alpha-azolylbenzyl)-1H-indoles. Bioorg Med Chem Lett 1999, 9, 3, 333. |
| 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) | 15292 | Indole; 1H-indole | 120-72-9 | C8H7N | 详情 | 详情 |
| (II) | 17263 | 4-fluorobenzoyl chloride | 403-43-0 | C7H4ClFO | 详情 | 详情 |
| (III) | 29518 | (4-fluorophenyl)(1H-indol-3-yl)methanone | C15H10FNO | 详情 | 详情 | |
| (IV) | 29519 | (1-ethyl-1H-indol-3-yl)(4-fluorophenyl)methanone | C17H14FNO | 详情 | 详情 | |
| (V) | 29520 | (1-ethyl-1H-indol-3-yl)(4-fluorophenyl)methanol | C17H16FNO | 详情 | 详情 | |
| (VI) | 11353 | 1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; N,N-Carbonyldiimidazole; 1,1'-Carbonylbis(1H-imidazole) | 530-62-1 | C7H6N4O | 详情 | 详情 |
Extended Information