CGP-11112
(E)-N-[2-[4-[(3-环己基-2-亚胺基-1-吡氮基苯基)磺酰]苯基]乙基]-2-丁烯酰Chemical Name: (E)-N-[2-[4-[(3-Cyclohexyl-2-imino-1-imidazolidinyl)sulfonyl]phenyl]ethyl]-2-butenamide; trans-1-[[p-[2-(Crotonylamino)ethyl]phenyl]sulfonyl]-3-cyclohexyl-2-iminoimidazolidine
CAS No. 85390-06-3
项目整合开发状态: Biological Testing
项目研究机构: Novartis (Originator)
合成路线:The condensation of 4-[2-(acetylamino)ethyl]benzenesulfonyl chloride (I) with 1-cyclohexyl-2-iminoimidazolidine (III) by means of NaOH in refluxing acetone gives 1-[[4-(2-acetamidoethyl)phenyl]sulfonyl]-3-cyclohexyl-2-iminoimidazolidine (III),which is hydrolyzed with refluxing 2N HCl yielding 1-[[4-(2-aminoethyl)phenyl]sulfonyl]-3-cyclohexyl-2-iminoimidazolidine (IV).Finally,this compound is acylated with crotonic anhydride (V) in dioxane.The starting products (I) and (II) are obtained as follows:1) The acetylation of 2-phenylethylamine (VI) with acetic anhydride gives N-(2-phenylethyl)acetamide (VII),which is sulfonated with chlorosulfonic acid yielding compound (I).2) The reductocondensation of cyclohexanone (IX) with ethylenediamine (VIII) gives N-cyclohexylethylenediamine (X),which is then cyclized with cyanogen chloride to compound (II).
📌 参考资料/链接：
参考文献标题:CGP-11112
文献作者:Serradell,M.N.; Castar,J.; Thorpe,P.J.
参考来源:Drugs Fut 1984,9(5),315
📄 详细内容
合成路线:The condensation of 4-[2-(acetylamino)ethyl]benzenesulfonyl chloride (I) with 1-cyclohexyl-2-iminoimidazolidine (III) by means of NaOH in refluxing acetone gives 1-[[4-(2-acetamidoethyl)phenyl]sulfonyl]-3-cyclohexyl-2-iminoimidazolidine (III),which is hydrolyzed with refluxing 2N HCl yielding 1-[[4-(2-aminoethyl)phenyl]sulfonyl]-3-cyclohexyl-2-iminoimidazolidine (IV).Finally,this compound is acylated with crotonic anhydride (V) in dioxane.The starting products (I) and (II) are obtained as follows:1) The acetylation of 2-phenylethylamine (VI) with acetic anhydride gives N-(2-phenylethyl)acetamide (VII),which is sulfonated with chlorosulfonic acid yielding compound (I).2) The reductocondensation of cyclohexanone (IX) with ethylenediamine (VIII) gives N-cyclohexylethylenediamine (X),which is then cyclized with cyanogen chloride to compound (II).
参考文献标题:Sulfonyliminoimidazolidines.A new clas of oral hypoglycemic agents.I.1-[[p-[2-(Acylamino)ethyl]phenyl]sulfonyl]-2-iminoimidazolidies
文献作者:Schweizer,E.H.; M鋜ki,F.; Lehmann,C.; Dietrich,H.
参考来源:J Med Chem 1983,26(7),964-970
产品链接: CAS No. 85390-06-3››