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【结 构 式】 
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【药物名称】O-Demethylmurrayafoline A 【化学名称】3,3'-Dimethyl[1,1'-bi-9H-carbazole]-2,2'-diol 【CA登记号】155519-83-8 【 分 子 式 】C26H20N2O2 【 分 子 量 】392.4615 |
【开发单位】Chinese Academy of Sciences (Originator), National Cancer Institute (Originator) 【药理作用】Oncolytic Drugs |
合成路线1
5-Methyl-2-nitrophenol (I) was protected as the benzyl ether (II) employing benzyl bromide and NaOH in DMSO. Reduction of the nitro group of (III) with iron and ammonium chloride afforded aniline (III), which was subsequently coupled with iodobenzene (IV) to furnish the diaryl amine (V). Cyclization of (V) in the presence of Pd(OAc)2 in refluxing AcOH gave rise to carbazole (VI). The benzyl group of (VI) was then removed by catalytic hydrogenation over Pd/C to yield phenol derivative (VII). Finally, the title compound was obtained by oxidative coupling of the phenolic monomer (VII) with di-tert-butyl peroxide in boiling chlorobenzene.
| 【1】 Zhang, A.; Lin, G.; The first synthesis of optically pure biscarbazoles and determination of their absolute configurations. Tetrahedron Lett 1999, 40, 2, 341. |
| 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) | 42182 | 5-methyl-2-nitrophenol | 700-38-9 | C7H7NO3 | 详情 | 详情 |
| (II) | 42183 | benzyl 5-methyl-2-nitrophenyl ether; 2-(benzyloxy)-4-methyl-1-nitrobenzene | C14H13NO3 | 详情 | 详情 | |
| (III) | 42184 | 2-(benzyloxy)-4-methylaniline; 2-(benzyloxy)-4-methylphenylamine | C14H15NO | 详情 | 详情 | |
| (IV) | 26344 | 1-Iodobenzene | 591-50-4 | C6H5I | 详情 | 详情 |
| (V) | 42185 | N-[2-(benzyloxy)-4-methylphenyl]-N-phenylamine; 2-(benzyloxy)-4-methyl-N-phenylaniline | C20H19NO | 详情 | 详情 | |
| (VI) | 42186 | benzyl 3-methyl-9H-carbazol-1-yl ether; 1-(benzyloxy)-3-methyl-9H-carbazole | C20H17NO | 详情 | 详情 | |
| (VII) | 42187 | 3-methyl-9H-carbazol-1-ol | C13H11NO | 详情 | 详情 |