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【结 构 式】 
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【药物名称】Cistinexine, Rec-15-1884 【化学名称】Dibenzyl[dithiobis[(R)-1-[[4,6-dibromo-alpha-(cyclohexylmethylamino)-o-tolyl]carbamoyl]ethylene]] dicarbamate 【CA登记号】86042-50-4 【 分 子 式 】C50H60Br4N6O6S2 【 分 子 量 】1224.8163 |
【开发单位】Recordati (Originator) 【药理作用】Antitussives, Expectorants, RESPIRATORY DRUGS, Treatment of Upper Respiratory Tract Disorders |
合成路线1
The reaction of cysteine (I) with benzyl chloroformate (II) in the usual way gives the corresponding di(benzyloxycarbonyl) derivative (III), which is treated with PCl5 or SOCl2 in CHCl3 to afford the bisacyl chloride (IV). Finally, this compound is condensed with 4,6-dibromo-2-(cyclohexylmethylaminomethyl) aniline (V) in ethyl acetate.
| 【1】 Giannini, E.H.; Farm Sci Ed 1985, 40, 2, 108-119. |
| 【2】 Nardi, D.; Tajana, A.; Motta, G.; Cazzulani, P.; Graziani, G. (Recordati Industria Chimica e Farmaceutica SpA); Therapeutically effective derivatives of cystine. DE 3225274; EP 0069527; FR 2509298; GB 2102792; JP 58032860; US 4438133 . |
| 【3】 Castaner, J.; Serradell, M.N.; Cistinexine. Drugs Fut 1986, 11, 3, 181. |
| 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) | 28171 | (2S)-2-amino-3-[[(2R)-2-amino-2-carboxyethyl]disulfanyl]propionic acid | 56-89-3 | C6H12N2O4S2 | 详情 | 详情 |
| (II) | 10101 | Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene | 501-53-1 | C8H7ClO2 | 详情 | 详情 |
| (III) | 28172 | (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[((2R)-2-[[(benzyloxy)carbonyl]amino]-2-carboxyethyl)disulfanyl]propionic acid | 6968-11-2 | C22H24N2O8S2 | 详情 | 详情 |
| (IV) | 27173 | (1R)-1-ethyl-2,2-dimethyl-3-butenyl 2-bromoacetate | C10H17BrO2 | 详情 | 详情 | |
| (V) | 28174 | 2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]aniline | C14H20Br2N2 | 详情 | 详情 |
Extended Information