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【结 构 式】 
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【药物名称】Sulconazole nitrate, RS-44872, Exelderm 【化学名称】(±)-1-[2,4-Dichloro-beta-[(p-chlorobenzyl)thio]phenethyl]imidazole mononitrate 【CA登记号】59293-82-2, 61318-91-0, 61318-90-9 (free base) 【 分 子 式 】C18H16Cl3N3O3S 【 分 子 量 】460.76952 |
【开发单位】Degussa (Originator), Roche Bioscience (Originator), Bioglan (Not Determined), Schwarz (Not Determined), Tanabe Seiyaku (Licensee), Westwood (Licensee) 【药理作用】Antifungal Agents, ANTIINFECTIVE THERAPY |
合成路线1
The reaction of 2,4-dichlorophenacyl chloride (I) with imidazole (A) gives the ketone (II), which is reduced with sodium borohydride to yield the alcohol (III). Conversion of the alcohol (III) to the chloro derivative (IV) with thionylchloride followed by reaction with p-chlorobenzyl mercaptan (V) affords sulconazole.
| 【1】 Keisu, E.E. U.; Manufacture of novel imidazole derivative. AT 347449B; BE 0833614; JP 59089667; ZA 7505100 . |
| 【2】 Arya, V.P.; Sulconazole. Drugs Fut 1980, 5, 4, 206. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 10255 | Imidazole; 1H-Imidazole | 288-32-4 | C3H4N2 | 详情 | 详情 |
| (I) | 31092 | 2,2',4'-trichloroacetophenone; 2-chloro-1-(2,4-dichlorophenyl)-1-ethanone | 4252-78-2 | C8H5Cl3O | 详情 | 详情 |
| (II) | 32200 | 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanone | 46503-52-0 | C11H8Cl2N2O | 详情 | 详情 |
| (III) | 14550 | 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanol; alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol; 1-(2',4'-Dichlorophenyl)-2-(1-imidazolyl)ethanol | 24155-42-8 | C11H10Cl2N2O | 详情 | 详情 |
| (IV) | 32673 | 1-[2-chloro-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole | C11H9Cl3N2 | 详情 | 详情 | |
| (V) | 32674 | (4-chlorophenyl)methanethiol; 4-chlorobenzylhydrosulfide | 6258-66-8 | C7H7ClS | 详情 | 详情 |