|
【结 构 式】 
|
【分子编号】22900 【品名】ethyl 6-([[2-(dimethylamino)ethyl]amino]carbonyl)-5-hydroxy-10-methoxybenzo[a]phenazine-9-carboxylate 【CA登记号】 |
【 分 子 式 】C25H26N4O5 【 分 子 量 】462.5054 【元素组成】C 64.92% H 5.67% N 12.11% O 17.3% |
合成路线1
该中间体在本合成路线中的序号：(V)NCU-190Na is synthesized by condensation of naphthoquinone (I) and phenylenediamine (II), but several isomers (IV) of benzo[a]phenazine are produced at the same time. Using ethyl chlorocarbonate, (III) is selectively produced and aminolysis of esters is also selective to the 6-position; thus, (V) is produced and can be converted to (VI) (NCU190Na). Various derivatives of (VI) can be synthesized in a similar manner. Compound (III) can also be prepared from naphthoquinone (I) and ethyl chloroformate (VII) to give ethyl 3-(ethoxycarbonyloxy)-1,4-dioxo-1,4-dihydro-2-naphthoate (VIII), which is condensed with phenylenediamine (II).
| 【1】 Watanabe, Y.; Soda, K.; Nakagami, J.; Sakakibara, Z.; Migita, Y.; Kumazawa, Y.; Selective synthsesis of new benzo(a)-phenazine-6-c. 108th Annu Meet Pharm Soc Jpn (April 4-7, Hiroshima) 1988, Abst 5E16 2-1. |
| 【2】 Kumazawa, Y.; Nakagami, J.; Soda, K.; Nakaike, S.; Sakakibara, Z.; Watanabe, Y.; Migita, Y.; Synthesis and antitumor activity of new benzo(a)-p. 108th Annu Meet Pharm Soc Jpn (April 4-7, Hiroshima) 1988, Abst 5E16 11-2. |
| 【3】 Migita, Y.; Eguchi, T.; Kumazawa, Y.; Nakagami, J.; Amano, T.; Sota, K.; Sakakibara, J. (Taisho Pharmaceutical Co., Ltd.); Benzo[a]phenazine derivs.. EP 0196910; ES 8706651; JP 1987000072; US 4686292 . |
| 【4】 Hoshi, A.; NCU-190Na. Drugs Fut 1988, 13, 8, 726. |
| 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) | 22896 | ethyl 3-hydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenecarboxylate | C13H10O5 | 详情 | 详情 | |
| (II) | 22897 | ethyl 4,5-diamino-2-methoxybenzoate | C10H14N2O3 | 详情 | 详情 | |
| (III) | 22898 | diethyl 5-hydroxy-10-methoxybenzo[a]phenazine-6,9-dicarboxylate | C23H20N2O6 | 详情 | 详情 | |
| (IV) | 22899 | diethyl 5-hydroxy-9-methoxybenzo[a]phenazine-6,10-dicarboxylate | C23H20N2O6 | 详情 | 详情 | |
| (V) | 22900 | ethyl 6-([[2-(dimethylamino)ethyl]amino]carbonyl)-5-hydroxy-10-methoxybenzo[a]phenazine-9-carboxylate | C25H26N4O5 | 详情 | 详情 | |
| (VII) | 11229 | 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate | 541-41-3 | C3H5ClO2 | 详情 | 详情 |
| (VIII) | 22902 | ethyl 3-[(ethoxycarbonyl)oxy]-1,4-dioxo-1,4-dihydro-2-naphthalenecarboxylate | C16H14O7 | 详情 | 详情 |