【结 构 式】 |
【药物名称】Deboxamet, ABC-85 【化学名称】5-Methoxy-2-methyl-3-indolylacetohydroxamic acid 【CA登记号】34024-41-4 【 分 子 式 】C12H14N2O3 【 分 子 量 】234.25698 |
【开发单位】Istituto Biologico Chemioterapico ABC (Originator) 【药理作用】Antiulcer Drugs, GASTROINTESTINAL DRUGS |
合成路线1
This compound can be obtained by three different ways: 1) The reaction of 1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetic acid (indomethacin) (I) with SOCl2 gives the corresponding acetyl chloride (II), which is treated with hydroxylamine hydrochloride and NaOH in water to afford 1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetohydroxamic acid (III). Finally, this compound is hydrolyzed with 0.5 N NaOH in water. 2) The reaction of 1-(p-chlorobenzoyl)-2-methyl-5-methoxy-3-indolylacetal-dehyde (IV) with N-hydroxybenzenesulfonamide (V) in DMSO by means of NaOH yields compound (III) already obtained. 3) By reaction of tert-butyl-5-methoxy-2-methyl-3-indolylacetate (VI) with hydroxylamine in methanol.
【1】 Tamietto, T.; Franzone, J.S.; De Martiis, F.; Sintesi e proprieta ntiflogistiche di alcuni acidi acetoidrossamici. Boll Chim Farm 1975, 114, 309-318. |
【2】 De Martiis, F.; Arrigoni-Martelli, E.; Tamietto, T.; US 3624103 . |
【3】 Tamietto, T.; US 4186133 . |
【4】 Serradell, M.N.; de Angelis, L.; Blancafort, P.; Castaner, J.; ABC-8/5. Drugs Fut 1982, 7, 6, 371. |
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) | 22930 | 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid | C19H16ClNO4 | 详情 | 详情 | |
(II) | 24047 | 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl chloride | C19H15Cl2NO3 | 详情 | 详情 | |
(III) | 37034 | 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-N-hydroxyacetamide | C19H17ClN2O4 | 详情 | 详情 | |
(IV) | 37035 | 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetaldehyde | C19H16ClNO3 | 详情 | 详情 | |
(V) | 37036 | N-hydroxybenzenesulfonamide | 599-71-3 | C6H7NO3S | 详情 | 详情 |
(VI) | 37038 | N-phenyl-N-[(1R,2R)-2-(1-pyrrolidinyl)cyclohexyl]amine; N-[(1R,2R)-2-(1-pyrrolidinyl)cyclohexyl]aniline | C16H24N2 | 详情 | 详情 |