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【结 构 式】 
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【药物名称】7-Methoxytacrine, 7-MEOTA 【化学名称】9-Amino-7-methoxy-1,2,3,4-tetrahydroacridine 【CA登记号】5778-80-3, 65239-02-3 (lactate) 【 分 子 式 】C14H16N2O 【 分 子 量 】228.29642 |
【开发单位】Purkyne Med. Res. Inst. (Originator) 【药理作用】Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, Acetylcholinesterase Inhibitors |
合成路线1
This compound can be prepared by two different methods: 1) By cyclocondensation of p-anisidine (I) with 2-oxocyclohexanecarboxylate (II) to 7-methoxy-1,2,3,4-tetrahydroacridone (III), which by treatment with refluxing POCl3 is converted to 9-chloro-7-methoxy-1,2,3,4-tetrahydroacridine (IV). This compound is converted to final product by treatment with NH3 in refluxing p-cresol. 2) By cyclocondensation of 5-methoxyisatin (V) and cyclohexanone (VI) in concentrated aqueous ammonia at 150 C to 7-methoxy-1,2,3,4-tetrahydroacridine-9-carboxamide (VII), followed by a Hoffman degradation with potassium hypobromite.
| 【1】 Sigal, M.V. Jr.; Brent, B.J.; Marchini, P.; 7,8,9,10-Tetrahalo-6H-cyclohepta[b]quinolines. US 3232945 . |
| 【2】 Bielavsky, J.; Analogues of 9-amino-1,2,3,4-tetrahydroacridine. Coll Czech Chem Commun 1977, 42, 2802-7. |
| 【3】 Dejmek, L.; 7-MEOTA. Drugs Fut 1990, 15, 2, 126. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 37678 | p-cresol | 106-44-5 | C7H8O | 详情 | 详情 | |
| (I) | 10478 | p-Anisidine; 4-Methoxyaniline; 4-Methoxyphenylamine | 104-94-9 | C7H9NO | 详情 | 详情 |
| (II) | 11889 | ethyl 2-oxocyclohexanecarboxylate; Ethyl 2-cyclohexanonecarboxylate | 1655-07-8 | C9H14O3 | 详情 | 详情 |
| (III) | 11890 | 7-Methoxy-1,3,4,10-tetrahydro-9(2H)-acridinone | C14H15NO2 | 详情 | 详情 | |
| (IV) | 11891 | 9-Chloro-5,6,7,8-tetrahydro-2-acridinyl methyl ether; 9-Chloro-7-methoxy-1,2,3,4-tetrahydroacridine | C14H14ClNO | 详情 | 详情 | |
| (V) | 11892 | 5-Methoxy-1H-indole-2,3-dione | 39755-95-8 | C9H7NO3 | 详情 | 详情 |
| (VI) | 11059 | Cyclohexanone | 108-94-1 | C6H10O | 详情 | 详情 |
| (VII) | 11894 | 7-Methoxy-1,2,3,4-tetrahydro-9-acridinecarboxamide | C15H16N2O2 | 详情 | 详情 |