Ferroquine, Ferrochloroquine, SSR-97193
二茂铁氯喹Chemical Name: 3-(7-Chloroquinolin-4-ylaminomethyl)-4-(dimethylaminomethyl)ferrocene
CAS No. 185055-67-8, 198057-42-0 (deleted CAS), 185055-70-3 (L-tartrate)
项目整合开发状态: Preclinical
项目研究机构: Universit?Sciences et Technol. Lille (Originator), Sanofi-Aventis (Not Determined)
合成路线:The (dimethylaminomethyl)ferrocene (I) was metalated with butyllithium and the organolithium intermediate (II) was condensed with dimethylformamide to furnish,after aqueous quenching,the ferrocenecarboxaldehyde (III).Aldehyde (III) was converted to oxime (IV) by treatment with hydroxylamine in aqueous ethanol.Reduction of oxime (IV) using LiAlH4 produced the primary amine (V).This was then condensed with 4,7-dichloroquinoline (VI) in hot NMP,and the resulting adduct was finally isolated as the L-tartrate salt.
📌 参考资料/链接：
参考文献标题:Antimalarial organometallic iron complexes
文献作者:Lebibi,J.; Brocard,J.; Maciejewski,L.(Universit?des Sciences et Technologies de Lille - Lille 1)
参考来源:WO 9635698
📄 详细内容
合成路线:The (dimethylaminomethyl)ferrocene (I) was metalated with butyllithium and the organolithium intermediate (II) was condensed with dimethylformamide to furnish,after aqueous quenching,the ferrocenecarboxaldehyde (III).Aldehyde (III) was converted to oxime (IV) by treatment with hydroxylamine in aqueous ethanol.Reduction of oxime (IV) using LiAlH4 produced the primary amine (V).This was then condensed with 4,7-dichloroquinoline (VI) in hot NMP,and the resulting adduct was finally isolated as the L-tartrate salt.
参考文献标题:In vitro antimalarial activity of a new organometallic analog,ferrocene-chloroquine
文献作者:Domarle,O.; Blampain,G.; Agnaniet,H.; Nzadiyabi,T.; Lebibi,J.; Brocard,J.; Maciejewski,L.; Biot,C.; Georges,A.J.; Millet,P.
参考来源:Antimicrob Agents Chemother 1998,42(3),540
合成路线:The (dimethylaminomethyl)ferrocene (I) was metalated with butyllithium and the organolithium intermediate (II) was condensed with dimethylformamide to furnish,after aqueous quenching,the ferrocenecarboxaldehyde (III).Aldehyde (III) was converted to oxime (IV) by treatment with hydroxylamine in aqueous ethanol.Reduction of oxime (IV) using LiAlH4 produced the primary amine (V).This was then condensed with 4,7-dichloroquinoline (VI) in hot NMP,and the resulting adduct was finally isolated as the L-tartrate salt.
参考文献标题:Synthesis an antimalarial activity in vitro and in vivo of a new ferrocene-chloroquine analogue
文献作者:Biot,C.; Glorian,G.; Maciejewski,L.A.; Brocard,J.S.
参考来源:J Med Chem 1997,40(23),3715
产品链接: CAS No. 185055-67-8››