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【结 构 式】

【药物名称】Topixantrone hydrochloride, BBR-3576, BBR-3409(dimaleate)

【化学名称】5-[2-(Dimethylamino)ethylamino]-2-[2-(2-hydroxyethylamino)ethyl]indazolo[4,3-gh]isoquinolin-6(2H)-one dihydrochloride

【CA登记号】156090-18-5 (free base)

【 分 子 式 】C21H28Cl2N6O2

【 分 子 量 】467.40231

【开发单位】Novuspharma (Originator)

【药理作用】Gastric Cancer Therapy, Oncolytic Drugs, Prostate Cancer Therapy, Solid Tumors Therapy, DNA-Intercalating Drugs

合成路线1

The synthesis of BBR-3409 has been described: The cyclization of 6-chloro-9-fluorobenz[g]isoquinoline-5,10-quinone (I) with 2-hydroxyethylhydrazine (II) in hot pyridine gives 2-(2-hydroxyethyl)-5-chloroindazolo[4,3-gh]isoquinolin-6(2H)-one (III), which is condensed with N-(2-aminoethyl)-N,N-dimethylamine (IV) in hot pyridine yielding the corresponding compound (V). The mesylation of the OH group of (V) with mesyl chloride and triethylamine in dichloromethane affords the mesylate (VI), which is condensed with hot ethanolamine (VII) to give BBR-3409.

1 Krapcho, A.P.; Menta, E.; Oliva, A.; Di Domenico, R.; Fiocchi, L.; Maresch, M.E.; Gallagher, C.E.; Hacker, M.P.; Beggiolin, G.; Giuliani, F.C.; Pezzoni, G.; Spinelli, S.; Synthesis and antitumor evaluation of 2,5-disubstituted-indazolo[4,3-gh]isoquinolin-6(2H)-ones (9-aza-anthrapyrazoles). J Med Chem 1998, 41, 27, 5429.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 24950 6-chloro-9-fluorobenzo[g]isoquinoline-5,10-dione C13H5ClFNO2 详情 详情
(II) 24951 2-hydrazino-1-ethanol 109-84-2 C2H8N2O 详情 详情
(III) 24952 5-chloro-2-(2-hydroxyethyl)indazolo[4,3-gh]isoquinolin-6(2H)-one C15H10ClN3O2 详情 详情
(IV) 14881 N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine 108-00-9 C4H12N2 详情 详情
(V) 26315 5-[[2-(dimethylamino)ethyl]amino]-2-(2-hydroxyethyl)indazolo[4,3-gh]isoquinolin-6(2H)-one C19H21N5O2 详情 详情
(VI) 26316 2-[5-[[2-(dimethylamino)ethyl]amino]-6-oxoindazolo[4,3-gh]isoquinolin-2(6H)-yl]ethyl methanesulfonate C20H23N5O4S 详情 详情
(VII) 10259 Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol;2-Aminoethyl alcohol 141-43-5 C2H7NO 详情 详情
Extended Information