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【结 构 式】 
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【药物名称】 【化学名称】10-[4-[4-(2-Hydroxyethyl)piperazin-1-yl]butyl]-2-methoxyacridin-9(10H)-one 【CA登记号】 【 分 子 式 】C24H31N3O3 【 分 子 量 】409.53297 |
【开发单位】Georgetown University (Originator), St. Jude Children's Res. Hosp. (Originator), University of Mysore (Originator), University of Tennessee, Memphis (Originator) 【药理作用】Modulators of the Therapeutic Activity of Antineoplastic Agents, Multidrug Resistance Modulators, ONCOLYTIC DRUGS |
合成路线1
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 |