【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% |
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 |