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【结 构 式】 
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【药物名称】 【化学名称】N-[2-[3-(2-Bromophenyl)ureido]-5-cyanophenyl]benzenesulfonamide 【CA登记号】182498-81-3 【 分 子 式 】C20H15BrN4O3S 【 分 子 量 】471.33555 |
【开发单位】GlaxoSmithKline (Originator) 【药理作用】Antipsoriatics, DERMATOLOGIC DRUGS, Chemokine CXCR2 (IL-8 beta Receptor) Antagonists |
合成路线1
The sulfonation of 3-aminobenzonitrile (I) with benzenesulfonyl chloride (II) by means of triethylamine in dichloromethane gives the sulfonamide (III), which is nitrated with HNO3 in acetic anhydride yielding 4-nitro-3-(phenyl sulfonamido)benzonitrile (IV). The reduction of (IV) with SnCl2 in hot ethanol affords the corresponding 4-amino derivative (V), which is finally condensed with 2-bromophenyl isocyanate (VI) in hot DMF.
| 【1】 Widdowson, K.L.; Veber, D.F.; Jurewicz, A.J.; Rutledge, M.C. Jr.; Hertzberg, R.P. (SmithKline Beecham plc); IL-8 receptor antagonists. EP 0809492; JP 1999503110; US 5780483; WO 9625157 . |
| 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) | 28662 | 3-aminobenzonitrile | 2237-30-1 | C7H6N2 | 详情 | 详情 |
| (II) | 14713 | benzenesulfonyl chloride | 98-09-9 | C6H5ClO2S | 详情 | 详情 |
| (III) | 28663 | N-(3-cyanophenyl)benzenesulfonamide | C13H10N2O2S | 详情 | 详情 | |
| (IV) | 28664 | N-(5-cyano-2-nitrophenyl)benzenesulfonamide | C13H9N3O4S | 详情 | 详情 | |
| (V) | 28665 | N-(2-amino-5-cyanophenyl)benzenesulfonamide | C13H11N3O2S | 详情 | 详情 | |
| (VI) | 28666 | 1-bromo-2-isocyanatobenzene | 1592-00-3 | C7H4BrNO | 详情 | 详情 |