【结 构 式】 |
【分子编号】32676 【品名】2-[(2-aminoethyl)amino]-1-ethanol 【CA登记号】111-41-1 |
【 分 子 式 】C4H12N2O 【 分 子 量 】104.15216 【元素组成】C 46.13% H 11.61% N 26.9% O 15.36% |
合成路线1
该中间体在本合成路线中的序号:(II)By condensation of 2,3-dihydro-1,4-dihydroxyanthraquinone (I) with N-(aminoethyl)ethanolamine (II) in refluxing ethanol, followed by oxidation with air and treatment with acetic acid.
【1】 Hoare, R.C.; DE 2734907 . |
【2】 Hoare, R.C.; US 4051155 . |
【3】 Hoare, R.C.; FR 2399244 . |
【4】 Wallace, R.E.; Durr, F.E.; Citarella, R.V.; Antitumor agents. 1. 1,4-Bis[(aminoalkyl)amino]-9,10-anthracenediones. J Med Chem 1979, 22, 9, 1024. |
【5】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Hillier, K.; Ametantrone acetate. Drugs Fut 1982, 7, 5, 303. |
合成路线2
该中间体在本合成路线中的序号:(II)By reaction of 5,8-dihydroxyleucoquinizarin (1,4,5,8-tetrahydroxy-9,10-anthraquinone) (I) with 2-(aminoethylamino)ethanol (II) in dioxane at 60 C.
【1】 Zee-Cheng, R.K.Y.; Cheng, C.C.; Antineoplastic agents. Structure-activity relationship study of bis(substituted aminoalkylamino)anthraquinones. J Med Chem 1978, 21, 3, 291-294. |
【2】 Blancafort, P.; Sweetman, A.J.; Castaner, J.; Serradell, M.N.; CL-232315. Drugs Fut 1980, 5, 5, 234. |
合成路线3
该中间体在本合成路线中的序号: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 |