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【结 构 式】

【药物名称】

【化学名称】N-[2-[3-(2-Bromophenyl)ureido]-5-cyanophenyl]benzenesulfonamide
      N-(2-Bromophenyl)-N'-[4-cyano-2-(phenylsulfonamido)phenyl]urea

【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
Extended Information