Halofantrine hydrochloride, SK&F-102866, WR-171669, Halfan
盐酸卤泛群 卤方特瑞 Chemical Name: (?-1,3-Dichloro-9-[3-(dibutylamino)-1-hydroxypropyl]-6-(trifluoromethyl)phenanthrene hydrochloride
CAS No. 36167-63-2, 69756-53-2 (free base), 66051-63-6 (racemic, free base)
项目整合开发状态: Launched-1988
项目研究机构: GlaxoSmithKline (Originator), Walter Reed Army Institute (Originator)
合成路线:The reduction of 1,3-dichloro-6-trifluoromethylphenanthrene-9-carboxylic acid (I) with BH3 in THF gives 1,3-dichloro-6-trifluoromethyl-9-hydroxymethylphenanthrene (II),which is oxidized with lead tetracetate in pyridine to yield 1,3-dichloro-6-trifluoromethylphenanthren-9-carboxaldehyde (III).The reaction of (III) with N,N-dibutylbromoacetamide (IV) by means of Zn in THF affords 1,3-dichloro-6-trifluoromethyl-9-[3-(dibutylamino)-3-oxo-1-hydroxypropyl]phenanthrene (V),which is finally reduced with BH3 as before,and treated with HCl.
📌 参考资料/链接：
参考文献标题:Halofantrine hydrochloride
文献作者:Hillier,K.; Castar,J.; Blancafort,P.; Serradell,M.N.
参考来源:Drugs Fut 1980,5(11),547
📄 详细内容
合成路线:The reduction of 1,3-dichloro-6-trifluoromethylphenanthrene-9-carboxylic acid (I) with BH3 in THF gives 1,3-dichloro-6-trifluoromethyl-9-hydroxymethylphenanthrene (II),which is oxidized with lead tetracetate in pyridine to yield 1,3-dichloro-6-trifluoromethylphenanthren-9-carboxaldehyde (III).The reaction of (III) with N,N-dibutylbromoacetamide (IV) by means of Zn in THF affords 1,3-dichloro-6-trifluoromethyl-9-[3-(dibutylamino)-3-oxo-1-hydroxypropyl]phenanthrene (V),which is finally reduced with BH3 as before,and treated with HCl.
参考文献标题:Antimalarial arylaminopropanols
文献作者:Colwell,W.T.; et al.
参考来源:J Med Chem 1972,15771-775
产品链接: CAS No. 36167-63-2›› 产品链接: CAS No.69756-53-2››