Nortopixantrone hydrochloride, BBR-3438

Chemical Name: 2-[2-(2-Hydroxyethylamino)ethyl]-5-[2-(methylamino)ethylamino]indazolo[4,3-gh]isoquinolin-6(2H)-one dihydrochloride
CAS No. 156090-17-4 (free base)
项目整合开发状态: Phase II
项目研究机构: Novuspharma (Originator), University of Vermont (Originator)
合成路线:The synthesis of BBR-3438 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-methylcarbamic acid tert-butyl ester (IV) in hot pyridine yielding the corresponding 5-[2-[N-(tert-butoxycarbonyl)-N-methylamino]ethylamino] derivative (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 the protected compound (VIII).Finally,this compound is deprotected with HCl yielding BBR-3438.

合成路线: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.