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【结 构 式】 
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【药物名称】 【化学名称】1-(4-Chlorophenyl)-3-(hydroxymethyl)-9H-pyrido[3,4-b]indole 【CA登记号】 【 分 子 式 】C18H13ClN2O 【 分 子 量 】308.77011 |
【开发单位】Central Drug Research Institute (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Treatment of Helminthic Diseases |
合成路线1
Esterification of L-tryptophan (I) by means of MeOH and SOCl2 gave the corresponding methyl ester (II). Subsequent Pictet-Spengler cyclization of (II) with 4-chlorobenzaldehyde (III) furnished the tetrahydropyridoindole (IV), which was dehydrogenated to the beta-carboline (V) using sulfur in refluxing xylene. The ester group of (V) was finally reduced to the target alcohol with LiAlH4 in THF.
| 【1】 Srivastava, S.K.; et al.; Potent 1,3-disubstituted-9H-pyrido[3,4-b]indoles as new lead compounds in antifilarial chemotherapy. J Med Chem 1999, 42, 9, 1667. |
| 【2】 Srivastava, S.K.; et al.; Potent 1,3-disubstituted-9H-pyrido[3,4-b]indoles as new lead compounds in antifilarial chemotherapy. Bioorg Med Chem 1999, 7, 6, 1223. |
| 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) | 30836 | L-tryptophan | 73-22-3 | C11H12N2O2 | 详情 | 详情 |
| (II) | 30837 | methyl (2S)-2-amino-3-(1H-indol-3-yl)propanoate | C12H14N2O2 | 详情 | 详情 | |
| (III) | 29029 | 4-chlorobenzaldehyde | 104-88-1 | C7H5ClO | 详情 | 详情 |
| (IV) | 30834 | methyl 1-(4-chlorophenyl)-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylate | C19H17ClN2O2 | 详情 | 详情 | |
| (V) | 30835 | methyl 1-(4-chlorophenyl)-9H-beta-carboline-3-carboxylate | C19H13ClN2O2 | 详情 | 详情 |
Extended Information