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【结 构 式】 
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【分子编号】31172 【品名】2-[2-(dimethylamino)ethyl]-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione 【CA登记号】 |
【 分 子 式 】C16H15N3O4 【 分 子 量 】313.31292 【元素组成】C 61.34% H 4.83% N 13.41% O 20.43% |
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：(III)This compound can be obtained by two related ways: 1) The reduction of 3-nitronaphthalene-1,8-dicarboxylic acid anhydride (I) with H2 over Pd/C in DMF gives the corresponding 3-amino-anhydride (II), which is then treated with N,N-dimethylethylenediamine in refluxing toluene or ethanol. (2,3) 2) The reaction of anhydride (I) with N,N-dimethylethylenediamine as before gives 2-[2-(dimethylamino)ethyl]-5-nitro-1H-benz[d,e]isoquinoline-1,3 (2H)-dione (III), which is reduced with H2 or HCOONH4 (4) over Pd/C , or with Sn-HCl at 90-100 C. (1)
| 【1】 Brana, M.F.; Martinez Sanz, A.; Perez Alvarez-Ossorio, R.; Martinez Roldan, C.; Rodan Fernandez de Gamboa, C. (Made Labs.); Naphthalimides, process for their preparation and pharmaceutical compositions containing them. DE 2823987 . |
| 【2】 Nishimura, N.; Askew, B.; Patel, V.F.; Elbaum, D.; Habgood, G.; Kim, J.L.; Handley, M.; Booker, S.; Germain, J.; Kim, T.-S.; Yuan, C.C. (Amgen Inc.); Substd. benzylamine derivs. and methods of use. US 2003134836; WO 0407457 . |
| 【3】 Castaner, J.; Castaner, R.M.; Eastland, G.; Amonafide. Drugs Fut 1990, 15, 9, 879. |
| 【4】 Zee-Cheng, R.K.Y.; Cheng, C.C.; N-(Aminoalkyl)imide antineoplastic agents. Synthesis and biological activity. J Med Chem 1985, 28, 9, 1216-22. |
| 【5】 Fernández Braña, M.; Martínez Sanz, A.; Castellano, J.M.; Martínez Roldan, C.; Roldan Fernández de Gamboa, C.; Synthesis and cytostatic activity of benz(de)isoquinolin-1,3-diones. Structure-activity relationships. Eur J Med Chem - Chim Ther 1981, 16, 3, 207-212. |
| 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) | 15864 | 5-nitro-1H,3H-benzo[de]isochromene-1,3-dione; 3-Nitro-1,8-naphthalic anhydride | 3027-38-1 | C12H5NO5 | 详情 | 详情 |
| (II) | 31171 | 5-amino-1H,3H-benzo[de]isochromene-1,3-dione | C12H7NO3 | 详情 | 详情 | |
| (III) | 31172 | 2-[2-(dimethylamino)ethyl]-5-nitro-1H-benzo[de]isoquinoline-1,3(2H)-dione | C16H15N3O4 | 详情 | 详情 |
Extended Information