• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】21210

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

【CA登记号】

【 分 子 式 】C14H6Cl2O3

【 分 子 量 】293.10524

【元素组成】C 57.37% H 2.06% Cl 24.19% O 16.38%

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)

1,4-Dichloro-5-hydroxy-9,10-anthracenedione (I) is alkylated with powdered potassium carbonate and benzyl bromide to give the ether (II). The ether is condensed with threee equivalents of 2-[(2-hydrazinoethyl)amino]ethanol in anhydrous dimethylsulfoxide to give regioisomers (III) and (IV), which are separated by flash silica gel chromatography. The isomer (III) is reacted with an excess of 2-[(2-aminoethyl)amino]ethanol in refluxing pyridine to give the intermediate (V). The intermediate is converted to the 10-hydroxy isomer by hydrogenolysis of the benzyl protecting group with Pearlman's catalyst in glacial acetic acid, followed by dihydrochloride salt formation.

1 Showalter, H.D.H.; Werbel, L.M.; Johnson, J.L.; Elslager, E.F. (Warner-Lambert Co.); Substituted anthra[1,9-cd]pyrazol-6(2H)-ones. EP 0103381 .
2 Eastland, G. Jr.; BIANTRAZOLE. Drugs Fut 1989, 14, 8, 742.
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
12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
27775 2-[(2-hydrazinoethyl)amino]-1-ethanol C4H13N3O 详情 详情
32676 2-[(2-aminoethyl)amino]-1-ethanol 111-41-1 C4H12N2O 详情 详情
(I) 21210 1,4-dichloro-5-hydroxyanthra-9,10-quinone C14H6Cl2O3 详情 详情
(II) 21211 5-(benzyloxy)-1,4-dichloroanthra-9,10-quinone C21H12Cl2O3 详情 详情
(III) 21212 7-(benzyloxy)-5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]dibenzo[cd,g]indazol-6(2H)-one C25H22ClN3O3 详情 详情
(IV) 21213 10-(benzyloxy)-5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]dibenzo[cd,g]indazol-6(2H)-one C25H22ClN3O3 详情 详情
(V) 21214 7-(benzyloxy)-2-[2-[(2-hydroxyethyl)amino]ethyl]-5-([2-[(2-hydroxyethyl)amino]ethyl]amino)dibenzo[cd,g]indazol-6(2H)-one C29H33N5O4 详情 详情
Extended Information