Biantrazole hydrochloride, Losoxantrone hydrochloride, DuP-941, NSC-357885, CI-941

合成路线: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.

参考文献标题:BIANTRAZOLE
文献作者:Eastland,G.Jr.
参考来源:Drugs Fut 1989,14(8),742


合成路线: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 玹wo armed?compound,which,followed by treatment with Pearlman's catalyst in glacial AcOH,gives the target compound CI-937.

合成路线: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.
参考文献标题:5-[(Aminoalkyl)amino]-substituted anthra[1,9-cd]pyrazol-6(2H)-ones as novel anticancer agents.Synthesis and biological evaluation
文献作者:Showalter,H.D.H.; Johnson,J.L.; Werbel,L.M.; Leopold,W.R.; Jackson,R.C.; Elslager,E.F.
参考来源:J Med Chem 1984,27(3),253-5