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【结 构 式】 
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【分子编号】57757 【品名】10-(4-chlorobutyl)-2-methoxy-9(10H)-acridinone 【CA登记号】 |
【 分 子 式 】C18H18ClNO2 【 分 子 量 】315.79916 【元素组成】C 68.46% H 5.75% Cl 11.23% N 4.44% O 10.13% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(VI)Ullmann condensation between o-chlorobenzoic acid (I) and p-anisidine (II) produces the diphenylamine carboxylic acid (III), which is further cyclized to the 2-methoxyacridone (IV) by heating in polyphosphoric acid. N-Alkylation of acridone (IV) with 1-bromo-4-chlorobutane (V) in the presence of KOH under phase-transfer conditions furnishes the N-(chlorobutyl)acridone (VI). Finally, nucleophilic substitution of the chloro group of (VI) with N-(2-hydroxyethyl)piperazine (VII) gives rise to the title compound.
| 【1】 Krishnegowda, G.; et al.; Synthesis and chemical characterization of 2-methoxy-N10-substituted acridones needed to reverse vinblastine resistance in multidrug resistant (MDR) cancer cells. Bioorg Med Chem 2002, 10, 7, 2367. |
| 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) | 10203 | o-Chlorobenzoic acid; 2-Chlorobenzoic acid | 118-91-2 | C7H5ClO2 | 详情 | 详情 |
| (II) | 10478 | p-Anisidine; 4-Methoxyaniline; 4-Methoxyphenylamine | 104-94-9 | C7H9NO | 详情 | 详情 |
| (III) | 57755 | 2-(4-methoxyanilino)benzoic acid | C14H13NO3 | 详情 | 详情 | |
| (IV) | 57756 | 2-Methoxy-9(10H)-acridone | C14H11NO2 | 详情 | 详情 | |
| (V) | 16141 | 1-bromo-4-chlorobutane | 6940-78-9 | C4H8BrCl | 详情 | 详情 |
| (VI) | 57757 | 10-(4-chlorobutyl)-2-methoxy-9(10H)-acridinone | C18H18ClNO2 | 详情 | 详情 | |
| (VII) | 21893 | 2-(1-piperazinyl)-1-ethanol; 1-piperazineethanol; 1-(2-Hydroxyethyl)piperazine | 103-76-4 | C6H14N2O | 详情 | 详情 |
Extended Information