【结 构 式】 |
【药物名称】Vinmegallate, RGH-4417 【化学名称】3alpha,16alpha-17,18-Didehydroeburnamenine-14-methanol 3,4,5-trimethoxybenzoate 【CA登记号】83482-77-3 【 分 子 式 】C30H32N2O5 【 分 子 量 】500.59994 |
【开发单位】Gedeon Richter (Originator) 【药理作用】Antipsoriatics, DERMATOLOGIC DRUGS |
合成路线1
Tabersonine (I), isolated from plant material, reacted with disuccinoyl peroxide in methanol - HCl - water gives the rearranged product (II). Dehydration of (II) with formic acid and acetyl chloride in CH2Cl2 yields the ester (III), which is reduced with LiAlH4 to the alcohol (IV). Finally, acylation with 3,4,5 trimethoxybenzoyl chloride (V) results in RGH-4417 (VI).
【1】 Keve, T.; et al. (Gedeon Richter Ltd.); Polycyclic compounds containing a double bond in the D-ring pharmaceutical compositions containing them and methods of treating psoriasis with them. DE 3204630; FR 2499572; GB 2094297; GB 2125788; HU 183323; JP 57181087; US 4424223 . |
【2】 Balazs, M.Z.; Nogradi, M.; Kiss, B.; RGH-4417. Drugs Fut 1986, 11, 8, 663. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 24672 | Tabersonine; Methyl 3a-ethyl-3a,4,6,11,12,13a-hexahydro-1H-indolizino[8,1-cd]carbazole-5-carboxylate | C21H24N2O2 | 详情 | 详情 | |
(II) | 24673 | methyl (13aR,13bS)-13a-ethyl-12-hydroxy-5,6,12,13,13a,13b-hexahydro-3H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate | C21H24N2O3 | 详情 | 详情 | |
(III) | 24674 | methyl (13aR,13bS)-13a-ethyl-5,6,12,13,13a,13b-hexahydro-3H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate | C21H24N2O2 | 详情 | 详情 | |
(IV) | 24675 | [(13aR,13bS)-13a-ethyl-5,6,12,13,13a,13b-hexahydro-3H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12-yl]methanol | C20H24N2O | 详情 | 详情 | |
(V) | 13571 | 3,4,5Ttrimethoxybenzoyl chloride | 4521-61-3 | C10H11ClO4 | 详情 | 详情 |
Extended Information