【药物名称】CY-208-243
化学结构式(Chemical Structure):
参考文献No.2740
标题:Indolophenanthidines, their preparation and use
作者:Hagenbach, A.; Seiler, M.P.; W黷hrich, H.J. (Novartis AG; Novartis Deutschland GmbH)
来源:DE 3402392; EP 0155903; ES 8606339; JP 1985197687; US 4634708
合成路线图解说明:

The condensation of 1-benzoyl-1,2,2a,3,4,5-hexahydrobenzo[c,d]indol-4-one (I) with methylamine followed by acylation of the resulting enamine with benzoyl chloride gives 1,N-dibenzoyl-4-(methylamino)-1,2,2a,3-tetrahydrobenzo[c,d]indole (II) which, by irradiation with UV light in acetone, is isomerized to (5aR*,6aS*,12bS*)-4-benzoyl-7-methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridin-8-one (III). The reduction of (III) with LiAlH4 in ether, followed by hydrolysis with NaOH, and optical resolution with (+)-mandelic acid affords (+)-(5aS,6aR,12bR)-7-methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridine (IV), which is finally dehydrogenated with MnO2 in methylene chloride.

参考文献No.106814
标题:CY-208-243
作者:Prous, J.; Casta馿r, J.
来源:Drugs Fut 1990,15(4),344
合成路线图解说明:

The condensation of 1-benzoyl-1,2,2a,3,4,5-hexahydrobenzo[c,d]indol-4-one (I) with methylamine followed by acylation of the resulting enamine with benzoyl chloride gives 1,N-dibenzoyl-4-(methylamino)-1,2,2a,3-tetrahydrobenzo[c,d]indole (II) which, by irradiation with UV light in acetone, is isomerized to (5aR*,6aS*,12bS*)-4-benzoyl-7-methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridin-8-one (III). The reduction of (III) with LiAlH4 in ether, followed by hydrolysis with NaOH, and optical resolution with (+)-mandelic acid affords (+)-(5aS,6aR,12bR)-7-methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridine (IV), which is finally dehydrogenated with MnO2 in methylene chloride.

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