N-[4-(3-cyclohexyl-2-imino-imidazolidine-1-sulfonyl)-phenethyl]-3-phenyl-acrylamide | 85390-12-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-[4-(3-cyclohexyl-2-imino-imidazolidine-1-sulfonyl)-phenethyl]-3-phenyl-acrylamide
• 英文别名: (E)-N-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]-3-phenylprop-2-enamide
• CAS: 85390-12-1
• 化学式: C₂₆H₃₂N₄O₃S
• 分子量: 480.631
• InChiKey: LUZUQJMOOFMGRU-WWPPMECYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  肉桂酸 、 1-<sulfonyl>-3-cyclohexyl-2-iminoimidazolidine 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.0h， 以56%的产率得到N-[4-(3-cyclohexyl-2-imino-imidazolidine-1-sulfonyl)-phenethyl]-3-phenyl-acrylamide
  参考文献：
  名称：

  Sulfonyliminoimidazolidines. A new class of oral hypoglycemic agents. 1. 1-[[p-[2-(Acylamino)ethyl]phenyl]sulfonyl]-2-iminoimidazolidines

  摘要：

  A series of 1-[[p-[2-(acylamino)ethyl]phenyl]sulfonyl]-2-iminoimidazolidines has been synthesized. Compounds from this new class of oral hypoglycemic agents lower blood glucose in normal and in streptozotocin-diabetic rats. Potent analogues were obtained by modification of the acyl residue. 1-[[p-[2-(Crotonylamino)ethyl]phenyl]-sulfonyl]-3-cyclohexyl-2-iminoimidazolidine (44) turned out to be the most potent compound in the normal rat (20 times tolbutamide), and 1-[[p-[2-(5-methylisoxazole-3-carboxamido)ethyl]phenyl]sulfonyl]-3-cyclohexyl-2-imino-imidazolidine (30) displayed the highest potency in the diabetic rat (similar to phenformin).

  DOI：

  10.1021/jm00361a006

文献信息

• SCHWEIZER, E. H.;MARKI, F.;LEHMANN, C.;DIETRICH, H., J. MED. CHEM., 1983, 26, N 7, 964-970
  作者：SCHWEIZER, E. H.、MARKI, F.、LEHMANN, C.、DIETRICH, H.

  DOI：——

  日期：——
• Sulfonyliminoimidazolidines. A new class of oral hypoglycemic agents. 1. 1-[[p-[2-(Acylamino)ethyl]phenyl]sulfonyl]-2-iminoimidazolidines
  作者：Ernst H. Schweizer、Fritz Maerki、Claude Lehmann、Henri Dietrich

  DOI：10.1021/jm00361a006

  日期：1983.7

  A series of 1-[[p-[2-(acylamino)ethyl]phenyl]sulfonyl]-2-iminoimidazolidines has been synthesized. Compounds from this new class of oral hypoglycemic agents lower blood glucose in normal and in streptozotocin-diabetic rats. Potent analogues were obtained by modification of the acyl residue. 1-[[p-[2-(Crotonylamino)ethyl]phenyl]-sulfonyl]-3-cyclohexyl-2-iminoimidazolidine (44) turned out to be the most potent compound in the normal rat (20 times tolbutamide), and 1-[[p-[2-(5-methylisoxazole-3-carboxamido)ethyl]phenyl]sulfonyl]-3-cyclohexyl-2-imino-imidazolidine (30) displayed the highest potency in the diabetic rat (similar to phenformin).