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【结 构 式】 
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【药物名称】Nufenoxole, Sc-27166 【化学名称】2-[3,3-Diphenyl-3-(2-methyl-1,3,4-oxadiazol-5-yl)propyl]-2-azabicyclo[2.2.2]octane 【CA登记号】57726-65-5 【 分 子 式 】C25H29N3O 【 分 子 量 】387.52938 |
【开发单位】Ono (Originator), Pfizer (Originator) 【药理作用】Antidiarrheal Agents, GASTROINTESTINAL DRUGS |
合成路线1
The reaction of N-(2-chloroethyl)-2-azabicyclo[2.2.2]octane (I) with diphenylacetonitrile (II) by means of KOH in refluxing methyl ethyl ketone gives 4-[2-azabicyclo[2.2.2]octan-2-yl]-2,2-diphenylbutyronitrile (III), which by reaction with NaN3 in DMF at 125 C is converted into 5-[1,1-diphenyl-3-(2-azabicyclo[2.2.2]octan-2-yl)propyl]-1H-tetrazole (IV). Finally, this compound is treated with refluxing acetic anhydride.
| 【1】 Adelstein, G.W.; Yen, C.H.; Dajani, E.Z.; Bianchi, R.G.; 3,3-Diphenyl-3-(2-alkyl-1,3,4-ozadiazol-5-yl)propylcycloalkylamine, a novel series of antidiarrheal agents. J Med Chem 1976, 19, 10, 1221-25. |
| 【2】 Adelstein, G.W. (Pharmacia Corp.); 1,1-Diaryl-1-oxadiazolalkylamines. DE 2514183; DE 2514229; FR 2265367; FR 2265376; GB 1456943; GB 1494943; JP 50135081; JP 50135086; US 3917615 . |
| 【3】 Castaner, J.; Hillier, K.; Nufenoxole. Drugs Fut 1978, 3, 7, 533. |
| 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) | 39972 | 2-(2-chloroethyl)-2-azabicyclo[2.2.2]octane | C9H16ClN | 详情 | 详情 | |
| (II) | 14493 | alpha-phenylbenzeneacetonitrile; 2,2-diphenylacetonitrile; Diphenylacetonitrile | 86-29-3 | C14H11N | 详情 | 详情 |
| (III) | 39973 | 4-(2-azabicyclo[2.2.2]oct-2-yl)-2,2-diphenylbutanenitrile | C23H26N2 | 详情 | 详情 | |
| (IV) | 39974 | 2-[3,3-diphenyl-3-(1H-1,2,3,4-tetraazol-5-yl)propyl]-2-azabicyclo[2.2.2]octane | C23H27N5 | 详情 | 详情 |