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【结 构 式】 
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【药物名称】NC-2100 【化学名称】5-(7-Benzyloxyquinolin-3-ylmethyl)thiazolidine-2,4-dione 【CA登记号】179068-64-5 【 分 子 式 】C20H16N2O3S 【 分 子 量 】364.42612 |
【开发单位】Nippon Chemiphar (Originator) 【药理作用】Antidiabetic Drugs, ENDOCRINE DRUGS, Type 2 Diabetes Mellitus, Agents for, PPARalpha Agonists, PPARgamma Agonists, Thiazolidinediones (Glitazones) |
合成路线1
Treatment of 3-nitro-7-hydroxyquinoline (I) with NaH and benzyl bromide (A) provides benzyloxyderivative (II), which is reduced with SnCl4 in HCl/EtOH to yield (III). Amine (III) is then converted into (IV) via the diazonium salt by treatment with NaNO2 in HCl followed by reaction with methyl acrylate (B) in presence of CuO. Cyclization of (IV) with thiourea in 2-methoxyethanol in presence of NaOAc affords imino-thiazolidinone (V), which is finally hydrolyzed with HCl and EtOH.
| 【1】 Nomura, Y.; Sakuma, S.; Masui, S. (Nippon Chemiphar Co., Ltd.); Quinoline deriv.. EP 0787725; JP 1997100280; US 5693651; WO 9612719 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 | |
| (A) | 12912 | 1-(Bromomethyl)benzene; Alpha-bromotoluene | 100-39-0 | C7H7Br | 详情 | 详情 |
| (B) | 14156 | methyl acrylate | 96-33-3 | C4H6O2 | 详情 | 详情 |
| (I) | 41511 | 3-nitro-7-quinolinol | C9H6N2O3 | 详情 | 详情 | |
| (II) | 41512 | 7-(benzyloxy)-3-nitroquinoline; benzyl 3-nitro-7-quinolinyl ether | C16H12N2O3 | 详情 | 详情 | |
| (III) | 41513 | 7-(benzyloxy)-3-quinolinamine; 7-(benzyloxy)-3-quinolinylamine | C16H14N2O | 详情 | 详情 | |
| (IV) | 41514 | methyl 3-[7-(benzyloxy)-3-quinolinyl]-2-chloropropanoate | C20H18ClNO3 | 详情 | 详情 | |
| (V) | 41515 | 5-[[7-(benzyloxy)-3-quinolinyl]methyl]-2-imino-1,3-thiazolidin-4-one | C20H17N3O2S | 详情 | 详情 |