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【结 构 式】 
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【药物名称】DMAMI 【化学名称】N-(3,5-Dimethyladamantan-1-yl)maleimide 【CA登记号】219135-20-3 【 分 子 式 】C16H21NO2 【 分 子 量 】259.35127 |
【开发单位】National Taipei College of Nursing (Originator), National Taiwan University (Originator), National Yang-Ming University (Originator), Veterans General Hospital-Taipei (Originator) 【药理作用】ONCOLYTIC DRUGS, Apoptosis Inducers |
合成路线1
1-Bromo-3,5-dimethyladamantane (I) is subjected to Ritter reaction with acetonitrile in the presence of H2SO4 to produce acetamide (II). This is further hydrolyzed to the aminoadamantane (III) employing NaOH in refluxing diethyleneglycol. Condensation of amine (III) with maleic anhydride (IV) leads to the maleamic acid (V), which is finally cyclized to the target maleimide upon heating in acetic anhydride in the presence of NaOAc.
| 【1】 Wang, J.J.; Chern, Y.-T.; Liu, T.-Y.; Chi, C.-W.; In vitro and in vivo growth inhibition of cancer cells by adamantylmaleimide derivatives. Anti-Cancer Drug Des 1998, 13, 7, 779. |
| 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) | 52352 | 1-bromo-3,5-dimethyltricyclo[3.3.1.1~3,7~]decane | C12H19Br | 详情 | 详情 | |
| (II) | 63743 | N-(3,5-dimethyltricyclo[3.3.1.1~3,7~]dec-1-yl)acetamide | C14H23NO | 详情 | 详情 | |
| (III) | 63744 | 3,5-dimethyltricyclo[3.3.1.1~3,7~]dec-1-ylamine; 3,5-dimethyltricyclo[3.3.1.1~3,7~]decan-1-amine | C12H21N | 详情 | 详情 | |
| (IV) | 11182 | 2,5-Furandione; Maleic anhydride | 108-31-6 | C4H2O3 | 详情 | 详情 |
| (V) | 63745 | 4-[(3,5-dimethyltricyclo[3.3.1.1~3,7~]dec-1-yl)amino]-4-oxo-2-butenoic acid | C16H23NO3 | 详情 | 详情 |