1,4-dichloro-5,8-dihydroxyanthra-9,10-quinone -Drug Synthesis Database

【结构式】

【分子编号】27773

【品名】1,4-dichloro-5,8-dihydroxyanthra-9,10-quinone

【CA登记号】

【分子式】C₁₄H₆Cl₂O₄

【分子量】309.10464

【元素组成】C 54.4% H 1.96% Cl 22.94% O 20.7%

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：(I)

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.

参考文献中间体

合成目标

【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

Extended Information