|
【结 构 式】 
|
【药物名称】Zidometacin 【化学名称】1-(p-Azidobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid 【CA登记号】62851-43-8 【 分 子 式 】C19H16N4O4 【 分 子 量 】364.36377 |
【开发单位】Pierrel (Originator) 【药理作用】Non-Steroidal Antiinflammatory Drugs |
合成路线1
The condensation of methyl 5-methoxy-2-methylindole-3-acetate (I) with p-nitrobenzoyl chloride (II) by means of NaH in toluene gives methyl 1-(p-nItrobenzoyl)-5-methoxy-2-methylindole-3-acetate (III), which is hydrolyzed with p-toluenesulfonic acid in refluxing acetic acid yielding the corresponding free acid (IV). The reduction of (IV) with H2 over Pd/C in methanol affords 1-(p-aminobenzoyl)-5-methoxy-2-methyl indole-3-acetic acid (V) , which is finally treated with NaNO2 and HCl in acetic acid, and with NaN3 in water.
| 【1】 Tricerri, S.; et al.; Synthesis and preliminary pharmacological data on zidometacin, a new anti-inflammatory compound. Eur J Med Chem 1979, 14, 181-183. |
| 【2】 Blancafort, P.; Serradell, M.N.; de Angelis, L.; Castaner, J.; Zidometacin. Drugs Fut 1979, 4, 11, 839. |
| 【3】 Tricerri, S.; Bianchetti, A.; DE 2722399 . |
| 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) | 39636 | methyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate | C13H15NO3 | 详情 | 详情 | |
| (II) | 18941 | p-nitrobenzoyl chloride; 4-nitrobenzoyl chloride | 122-04-3 | C7H4ClNO3 | 详情 | 详情 |
| (III) | 39637 | methyl 2-[5-methoxy-2-methyl-1-(4-nitrobenzoyl)-1H-indol-3-yl]acetate | C20H18N2O6 | 详情 | 详情 | |
| (IV) | 39638 | 2-[5-methoxy-2-methyl-1-(4-nitrobenzoyl)-1H-indol-3-yl]acetic acid | C19H16N2O6 | 详情 | 详情 | |
| (V) | 39639 | 2-[1-(4-aminobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid | C19H18N2O4 | 详情 | 详情 |
Extended Information