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【结 构 式】 
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【药物名称】 【化学名称】2-[2-(Dimethylamino)ethyl]-6-[2-(dimethylamino)ethylamino]-8,11-dihydroxy-3,7-dihydro-2H-dibenzo[de,h]cinnoline-3,7-dione 【CA登记号】 【 分 子 式 】C23H27N5O4 【 分 子 量 】437.50274 |
【开发单位】Università degli Studi di Camerino (Originator), Politechnika Gdanska (Licensee) 【药理作用】ONCOLYTIC DRUGS, DNA-Damaging Drugs |
合成路线1
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 |