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【结 构 式】 
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【药物名称】 【化学名称】N-(5-Chloro-3-methoxypyrazin-2-yl)-5-(dimethylamino)naphthalene-1-sulfonamide 【CA登记号】173253-74-2 【 分 子 式 】C17H17ClN4O3S 【 分 子 量 】392.86704 |
【开发单位】AstraZeneca (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Endothelin ETA Receptor Antagonists, Endothelin Receptor Antagonists |
合成路线1
Bromination of 2-amino-5-chloropyrazine (I) with bromine in chloroform-pyridine provided bromopyrazine (II). Then, reaction with sodium methoxide in refluxing methanol afforded methyl ether (III). Finally, condensation of (III) with dansyl chloride (IV) in the presence of NaH in dimethoxyethane yielded the corresponding sulfonamide.
| 【1】 Hunt, S.J.; Tang, E.K.; James, R.; Heys, C.; Sumner, N.F.; Whiting, E.; Telford, B.; Dennis, M.; Mortlock, A.A.; Bath, C.; Wilson, C.; Butlin, R.J.; Bradbury, R.H.; New non-peptide endothelin-A receptor antagonists: Synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N-pyridyl-, -N-pyrimidinyl-, -N-pyridazinyl-, and -N-pyrazinyl-1-naphthalenesulfonamides. J Med Chem 1997, 40, 6, 996. |
| 【2】 Bradbury, R.H. (AstraZeneca plc); N-Heterocyclyl sulphonamide derivs. and their use as endothelin antagonists. EP 0752986; JP 1997510987; US 6083951; WO 9526957 . |
| 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) | 19024 | 5-chloro-2-pyrazinylamine; 5-chloro-2-pyrazinamine | C4H4ClN3 | 详情 | 详情 | |
| (II) | 19025 | 3-bromo-5-chloro-2-pyrazinylamine; 3-bromo-5-chloro-2-pyrazinamine | C4H3BrClN3 | 详情 | 详情 | |
| (III) | 19026 | 5-chloro-3-methoxy-2-pyrazinylamine; 5-chloro-3-methoxy-2-pyrazinamine | C5H6ClN3O | 详情 | 详情 | |
| (IV) | 19027 | 5-(dimethylamino)-1-naphthalenesulfonyl chloride | 605-65-2 | C12H12ClNO2S | 详情 | 详情 |
Extended Information