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【结 构 式】 
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【分子编号】63406 【品名】8,11-bis(benzyloxy)-6-chloro-2-[2-(dimethylamino)ethyl]-3H-dibenzo[de,h]cinnoline-3,7(2H)-dione 【CA登记号】 |
【 分 子 式 】C33H28ClN3O4 【 分 子 量 】566.05584 【元素组成】C 70.02% H 4.99% Cl 6.26% N 7.42% O 11.31% |
合成路线1
该中间体在本合成路线中的序号：(VI)Treatment of 1,4-di(benzyloxy)-5,8-dichloro-9,10-dihydro-9,10-anthracenedione (I) with CuCN in hot DMA results in the desired monosubstituted derivative (II). Subsequent basic hydrolysis of the nitrile group of (II) leads to carboxylic acid (III). After conversion of (III) into the corresponding acid chloride (IV) by means of PCl5, reaction with 2-(dimethylamino)ethylhydrazine (V) produces the tetracyclic compound (VI). Displacement of the remaining chloride of (VI) with 2-(dimethylamino)ethylamine (VII) in DMA then gives (VIII). The protecting benzyl groups of (VIII) are finally removed with trifluoroacetic acid to furnish the title compound.
| 【1】 Stefanska, B.; Arciemiuk, M.; Bontemps-Gracz, M.M.; Dzieduszycka, M.; Kupiec, A.; Martelli, S.; Borowski, E.; Synthesis and biological evaluation of 2,7-dihydro-3H-dibenzo[de,h]cinnoline-3,7-dione derivatives, a novel group of anticancer agents active on a multidrug resistant cell line. Bioorg Med Chem 2003, 11, 4, 561. |
| 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) | 27774 | 1,4-bis(benzyloxy)-5,8-dichloroanthra-9,10-quinone | C28H18Cl2O4 | 详情 | 详情 | |
| (II) | 63403 | 5,8-bis(benzyloxy)-4-chloro-9,10-dioxo-9,10-dihydro-1-anthracenecarbonitrile | C29H18ClNO4 | 详情 | 详情 | |
| (III) | 63404 | 5,8-bis(benzyloxy)-4-chloro-9,10-dioxo-9,10-dihydro-1-anthracenecarboxylic acid | C29H19ClO6 | 详情 | 详情 | |
| (IV) | 63405 | 5,8-bis(benzyloxy)-4-chloro-9,10-dioxo-9,10-dihydro-1-anthracenecarbonyl chloride | C29H18Cl2O5 | 详情 | 详情 | |
| (V) | 41186 | N-(2-hydrazinoethyl)-N,N-dimethylamine; 2-hydrazino-N,N-dimethyl-1-ethanamine | C4H13N3 | 详情 | 详情 | |
| (VI) | 63406 | 8,11-bis(benzyloxy)-6-chloro-2-[2-(dimethylamino)ethyl]-3H-dibenzo[de,h]cinnoline-3,7(2H)-dione | C33H28ClN3O4 | 详情 | 详情 | |
| (VII) | 14881 | N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine | 108-00-9 | C4H12N2 | 详情 | 详情 |
| (VIII) | 63407 | 8,11-bis(benzyloxy)-2-[2-(dimethylamino)ethyl]-6-{[2-(dimethylamino)ethyl]amino}-3H-dibenzo[de,h]cinnoline-3,7(2H)-dione | C37H39N5O4 | 详情 | 详情 |