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【结 构 式】 
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【药物名称】Moxantrazole, Teloxantrone, DuP-937, CI-937, PD-113309, NSC-355644 【化学名称】7,10-Dihydroxy-2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[[2-(methylamino)ethyl]amino]anthra[1,9-cd]pyrazol-6(2H)-one 【CA登记号】91441-48-4, 132937-88-3 (diHCl salt, monohydrate), 91450-82-7 (HBr salt) 【 分 子 式 】C21H25N5O4 【 分 子 量 】411.4645 |
【开发单位】Pfizer (Originator), Bristol-Myers Squibb (Licensee) 【药理作用】ONCOLYTIC DRUGS, DNA Topoisomerase II Inhibitors, DNA-Intercalating Drugs |
合成路线1
Treatment of 1,4-dichloro-5,8-dihydroxy-9,10-anthracenedione (I) with K2CO3 and benzyl bromide gives the benzyl ether (II) in refluxing acetone, which, followed by treatment with 2-[(2-hydrazinoethyl)amino]ethanol in anhydrous Me2SO, gives product (III). Treatment of product (III) with excess [(2-aminoethyl)amino]methane in refluxing pyridine gives the «two armed» compound, which, followed by treatment with Pearlman's catalyst in glacial AcOH, gives the target compound CI-937.
| 【1】 Proc Amer Assoc Cancer Res 1984, 25, 1, 352. |
| 【2】 Hoshi, A.; CI-937 and CI-942. Drugs Fut 1986, 11, 3, 179. |
| 【3】 Showalter, H.D.H.; Johnson, J.L.; Werbel, L.M.; Leopold, W.R.; Jackson, R.C.; Elslager, E.F.; 5-[(Aminoalkyl)amino]-substituted anthra[1, 9-cd]pyrazol-6(2H)-ones as novel anticancer agents. Synthesis and biological evaluation. J Med Chem 1984, 27, 3, 253-5. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 27775 | 2-[(2-hydrazinoethyl)amino]-1-ethanol | C4H13N3O | 详情 | 详情 | |
| (B) | 27777 | N-(2-aminoethyl)-N-methylamine | 109-81-9 | C3H10N2 | 详情 | 详情 |
| (I) | 27773 | 1,4-dichloro-5,8-dihydroxyanthra-9,10-quinone | C14H6Cl2O4 | 详情 | 详情 | |
| (II) | 27774 | 1,4-bis(benzyloxy)-5,8-dichloroanthra-9,10-quinone | C28H18Cl2O4 | 详情 | 详情 | |
| (III) | 27776 | 7,10-bis(benzyloxy)-5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]dibenzo[cd,g]indazol-6(2H)-one | C32H28ClN3O4 | 详情 | 详情 |