N-(2'-aminophenyl)-2-cyclohexyl-2-phenylacetamide | 862898-28-0

• 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: N-(2'-aminophenyl)-2-cyclohexyl-2-phenylacetamide
• 英文别名: N-(2-aminophenyl)-2-cyclohexyl-2-phenylacetamide
• CAS: 862898-28-0
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: OHTLHZMYWHNNJG-UHFFFAOYSA-N

物化性质

• 熔点：
  202 °C
• 沸点：
  527.8±43.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2'-aminophenyl)-2-cyclohexyl-2-phenylacetamide 在 对甲苯磺酸 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 92.0h， 生成 2-(cyclopentylphenyl)methyl-1H-benzimidazole
  参考文献：
  名称：

  将位阻二酰基化的1,2-苯二胺转化为2-取代的苯并咪唑。

  摘要：

  设计了一系列大体积的2-取代的苯并咪唑，以便为几个生物学靶标找到新的潜在客户。由它们的单酰化的对应物通过环脱水形成显示出强烈地依赖于酰基的性质。在二环己基甲基的情况下，仅在对称二酰基化前体的对甲苯磺酸/甲苯混合物中观察到环化。从混合二酰化衍生物开始分析机理。

  DOI：

  10.1248/cpb.53.492
• 作为产物：
  描述：

  α-环己基苯乙酸 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 N-(2'-aminophenyl)-2-cyclohexyl-2-phenylacetamide
  参考文献：
  名称：

  Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes

  摘要：

  Imidazoline derivatives have been reported to show anti hyperglycemic activity in vivo. In the present study, we first showed that there was no correlation between the in vivo antidiabetic activity and the in vitro affinities for the I-1/I-2 binding sites for several substituted daryl imidazolines. Among these compounds, 2-(alpha-cyclohexyl-benzyl)-4,5-dihydro-1H-imidazole 2 exhibited potent antihyperglycemic properties. It was then chosen as lead compound. Thirty-six new derivatives were synthesized by replacing the cyclohexyl/benzyl group by various cyclic systems or the imidazoline ring by isosteric heterocycles. These compounds were evaluated in vivo for their antihyperglycemic activity using an oral glucose tolerance test (OGTT) in a rat model of type-2 diabetes obtained by giving a single intravenous (iv) injection of a low dose of streptozotocin to rats (STZ rats) and in normal rats. Nine compounds with an imidazoline moiety, possibly substituted by a methyl group, had a potent effect on the glucose tolerance in normal or STZ-diabetic rats, after an oral (po) administration of the test compound at a dose of 30 or 10 mg kg(-1) without any hypoglycemia. Replacement of the imidazoline ring by isosteric heterocycles resulted in a total loss of activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.026

文献信息

• Synthesis and biological evaluation of benzimidazole derivatives as potent AMP-activated protein kinase activators
  作者：Julie Charton、Sophie Girault-Mizzi、Marie-Ange Debreu-Fontaine、Fabienne Foufelle、Isabelle Hainault、Jean-Guy Bizot-Espiard、Daniel-Henri Caignard、Christian Sergheraert

  DOI：10.1016/j.bmc.2006.02.028

  日期：2006.7

  Design, synthesis and structure-activity relationships of beU:/AP/DTD501/BMC/4818nzimidazole derivatives as activators of the AMP-activated protein kinase (AMPK) are presented in this paper. AMPK is the central component of a protein kinase cascade that plays a key role in the regulation of energy balance. Once activated, AMPK initiates a series of responses that are aimed at restoring the energy balance of the cell and recent studies have indicated that AMPK plays an important role in regulation of the whole-body energy metabolism. The following study based on the lead compound S27847 involved modification of three regions of this compound. Preliminary structure activity relationships are being described. (c) 2006 Elsevier Ltd. All rights reserved.
• Conversion of Sterically Hindered Diacylated 1,2-Phenylenediamines into 2-Substituted Benzimidazoles
  作者：Julie Charton、Sophie Girault-Mizzi、Christian Sergheraert

  DOI：10.1248/cpb.53.492

  日期：——

  for several biological targets. Formation by cyclodehydration from their monoacylated counterparts was shown to be strongly dependent upon the nature of the acyl group. In the case of a dicyclohexylmethyl group, cyclization was only observed in a p-toluenesulfonic acid/toluene mixture from the symmetrical diacylated precursor. Analysis of the mechanism was begun starting from mixed diacylated derivatives

  设计了一系列大体积的2-取代的苯并咪唑，以便为几个生物学靶标找到新的潜在客户。由它们的单酰化的对应物通过环脱水形成显示出强烈地依赖于酰基的性质。在二环己基甲基的情况下，仅在对称二酰基化前体的对甲苯磺酸/甲苯混合物中观察到环化。从混合二酰化衍生物开始分析机理。
• Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes
  作者：Louis Crane、Maria Anastassiadou、Salomé El Hage、Jean Luc Stigliani、Geneviève Baziard-Mouysset、Marc Payard、Jean Michel Leger、Jean-Guy Bizot-Espiard、Alain Ktorza、Daniel-Henri Caignard、Pierre Renard

  DOI：10.1016/j.bmc.2006.07.026

  日期：2006.11

  Imidazoline derivatives have been reported to show anti hyperglycemic activity in vivo. In the present study, we first showed that there was no correlation between the in vivo antidiabetic activity and the in vitro affinities for the I-1/I-2 binding sites for several substituted daryl imidazolines. Among these compounds, 2-(alpha-cyclohexyl-benzyl)-4,5-dihydro-1H-imidazole 2 exhibited potent antihyperglycemic properties. It was then chosen as lead compound. Thirty-six new derivatives were synthesized by replacing the cyclohexyl/benzyl group by various cyclic systems or the imidazoline ring by isosteric heterocycles. These compounds were evaluated in vivo for their antihyperglycemic activity using an oral glucose tolerance test (OGTT) in a rat model of type-2 diabetes obtained by giving a single intravenous (iv) injection of a low dose of streptozotocin to rats (STZ rats) and in normal rats. Nine compounds with an imidazoline moiety, possibly substituted by a methyl group, had a potent effect on the glucose tolerance in normal or STZ-diabetic rats, after an oral (po) administration of the test compound at a dose of 30 or 10 mg kg(-1) without any hypoglycemia. Replacement of the imidazoline ring by isosteric heterocycles resulted in a total loss of activity. (c) 2006 Elsevier Ltd. All rights reserved.