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【结 构 式】 
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【药物名称】Fenticonazole nitrate, Rec-151476B free base, Rec-151476, Lomexin 【化学名称】(±)-1-[2-(2,4-Dichlorophenyl)-2-[[4-(phenylthio)phenyl]methoxy]ethyl]-1H-imidazole mononitrate 【CA登记号】73151-29-8, 72479-26-6 (free base) 【 分 子 式 】C24H21Cl2N3O4S 【 分 子 量 】518.42267 |
【开发单位】Recordati (Originator), SK Pharma (Not Determined), Effik (Licensee), Gerot (Licensee), Pfizer (Licensee) 【药理作用】Antifungal Agents, ANTIINFECTIVE THERAPY |
合成路线1
The reduction of 2,4-dichlorophenacyl chloride with NaBH4 gives 1-(2,4-dichlorophenyl)-2-chloroethanol (II), which is condensed with imidazole (III) to yield 1-(2,4-dichlorophenyl)-2-(N-imidazolyl)ethanol (IV). Finally, this compound is condensed with 4-(phenylthio)benzyl chloride (V) [prepared by chloromethylation of diphenyl sulfide (VI) with formaldehyde and HCl] using NaH as condensing agent.
| 【1】 Cova, A.; Tajana, A.; Nardi, D.; Cappelleti, R.; Sibilia, C.; Physico-chemical, structural and analytical studies on fenticonazole, a new drug with antimycotic properties. Arzneim-Forsch Drug Res 1981, 31, 12, 2127. |
| 【2】 Nardi, D.; Massarani, E.; Tajana, A.; Veronese, M. (Recordati Industria Chimica e Farmaceutica SpA); Substituted dibenzyl ethers and parmaceutical compositions containing said ethers for the treatment of infections. DE 2917244; FR 2426047; GB 2025395; US 4221803 . |
| 【3】 Blancafort, P.; Castaner, J.; Serradell, M.N.; Fenticonazole Nitrate. Drugs Fut 1983, 8, 9, 767. |
| 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) | 31092 | 2,2',4'-trichloroacetophenone; 2-chloro-1-(2,4-dichlorophenyl)-1-ethanone | 4252-78-2 | C8H5Cl3O | 详情 | 详情 |
| (II) | 31093 | 2-chloro-1-(2,4-dichlorophenyl)-1-ethanol | 13692-14-3 | C8H7Cl3O | 详情 | 详情 |
| (III) | 10255 | Imidazole; 1H-Imidazole | 288-32-4 | C3H4N2 | 详情 | 详情 |
| (IV) | 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 |
| (V) | 31094 | 1-(chloromethyl)-4-(phenylsulfanyl)benzene; 4-(chloromethyl)phenyl phenyl sulfide | C13H11ClS | 详情 | 详情 | |
| (VI) | 23188 | 1-(phenylsulfanyl)benzene; diphenyl sulfide | 139-66-2 | C12H10S | 详情 | 详情 |