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【结 构 式】

【药物名称】Deboxamet, ABC-85

【化学名称】5-Methoxy-2-methyl-3-indolylacetohydroxamic acid
      5-Methoxy-2-methylindole-3-acetohydroxamic acid
      N-Hydroxy-5-methoxy-2-methyl-1H-indole-3-acetamide

【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
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