trans-1--phenylsulfonyl>-3-cyclohexyl-2-imino-imidazolidine | 85390-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-1--phenylsulfonyl>-3-cyclohexyl-2-imino-imidazolidine
• 英文别名: 1--phenylsulfonyl>-3-cyclohexyl-2-iminoimidazolidine；1-({p-[2-(crotonylamino)ethyl]phenyl}sulfonyl)-3-cyclohexyl-2-iminoimidazolidine；2-Butenamide, N-(2-(4-((3-cyclohexyl-2-imino-1-imidazolidinyl)sulfonyl)phenyl)ethyl)-, (2E)-；(E)-N-[2-[4-(3-cyclohexyl-2-iminoimidazolidin-1-yl)sulfonylphenyl]ethyl]but-2-enamide
• CAS: 85390-06-3
• 化学式: C₂₁H₃₀N₄O₃S
• 分子量: 418.56
• InChiKey: OSLWHOALCCNLIC-KFURWHPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  巴豆酸 、 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60%的产率得到trans-1--phenylsulfonyl>-3-cyclohexyl-2-imino-imidazolidine
  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

• Antidiabetic iminosulphonamides
  申请人：Ciba-Geigy Corporation

  公开号：US04591597A1

  公开（公告）日：1986-05-27

  The compounds of the formula ##STR1## in which R represents the radical of the formula ##STR2## in which R.sub.1 represents lower alkyl and each of R.sub.2 and R.sub.3, independently of the other, represents hydrogen or lower alkyl, and salts thereof exhibit antidiabetic actions.

  公式为##STR1##的化合物，其中R代表公式##STR2##的基团，其中R.sub.1代表较低的烷基，R.sub.2和R.sub.3各自独立地代表氢或较低的烷基，以及其盐，具有抗糖尿病作用。
• 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：——
• Iminosulfonamide und Verfahren zu ihrer Herstellung, die pharmazeutische Präparate solche Verbindungen enthalten, sowie die Verbindungen zur Verwendung
  申请人：CIBA-GEIGY AG

  公开号：EP0124479B1

  公开（公告）日：1988-01-20
• US4591597A
  申请人：——

  公开号：US4591597A

  公开（公告）日：1986-05-27
• 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).