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【结 构 式】 
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【药物名称】Ferroquine, Ferrochloroquine, SSR-97193 【化学名称】3-(7-Chloroquinolin-4-ylaminomethyl)-4-(dimethylaminomethyl)ferrocene 【CA登记号】185055-67-8, 198057-42-0 (deleted CAS), 185055-70-3 (L-tartrate) 【 分 子 式 】C23H24ClFeN3 【 分 子 量 】433.76783 |
【开发单位】Université Sciences et Technol. Lille (Originator), Sanofi-synthélabo (Not Determined) 【药理作用】ANTIINFECTIVE THERAPY, Antimalarials, Treatment of Protozoal Diseases |
合成路线1
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.
| 【1】 Domarle, O.; et al.; In vitro antimalarial activity of a new organometallic analog, ferrocene-chloroquine. Antimicrob Agents Chemother 1998, 42, 3, 540. |
| 【2】 Biot, C.; et al.; Synthesis an antimalarial activity in vitro and in vivo of a new ferrocene-chloroquine analogue. J Med Chem 1997, 40, 23, 3715. |
| 【3】 Lebibi, J.; Brocard, J.; Maciejewski, L. (Université des Sciences et Technologies de Lille - Lille 1); Antimalarial organometallic iron complexes. WO 9635698 . |