2-[Cyclohexyl(phenyl)methyl]-4,5-dihydro-1h-imidazole | 208718-02-9

• 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: 2-[Cyclohexyl(phenyl)methyl]-4,5-dihydro-1h-imidazole
• CAS: 208718-02-9
• 化学式: C₁₆H₂₂N₂
• 分子量: 242.364
• InChiKey: IOYSTCGWDOEPLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  环己基苯基乙腈 、 乙二胺 在 tetraphosphorus decasulfide 作用下， 反应 4.0h， 以41%的产率得到2-[Cyclohexyl(phenyl)methyl]-4,5-dihydro-1h-imidazole
  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

• Imidazoline compounds
  申请人：——

  公开号：US20040087638A1

  公开（公告）日：2004-05-06

  Compounds of formula (I): 1 wherein: R 1 represents an optionally substituted heteroaryl group, R 2 represents an optionally substituted cycloalkyl group, R 3 represents a hydrogen atom or an alkyl group, and R 4 and R 5 are as defined in the description, and Medicinal products containing the same are useful in the treatment of non-insulin-dependent type II diabetes, obesity, type I diabetes, hyperlipidaemia, hypercholesterolaemia and cardiovascular complications thereof.

  化合物的化学式（I）：其中：R1代表一个可选取代的杂环芳基团，R2代表一个可选取代的环烷基团，R3代表一个氢原子或一个烷基团，而R4和R5如描述中所定义，并且含有相同化合物的药物制剂在治疗非胰岛素依赖性2型糖尿病、肥胖症、1型糖尿病、高脂血症、高胆固醇血症及其心血管并发症方面是有用的。
• Dérivés de l'imidazoline, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：LES LABORATOIRES SERVIER

  公开号：EP1413579A1

  公开（公告）日：2004-04-28

  Composés de formule (I) : dans laquelle : R1 représente un groupement hétéroaryle éventuellement substitué, R2 représente un groupement cycloalkyle éventuellement substitué, R3 représente un atome d'hydrogène ou un groupement alkyle, R4 et R5sont tels que définis dans la description, leurs énantiomères, diastéréoisomères, tautomères, ainsi que leurs sels d'addition à un acide ou à une base pharmaceutiquement acceptable.

  式(I)化合物 其中： R1 代表任选取代的杂芳基、 R2 代表任选取代的环烷基 R3 代表氢原子或烷基、 R4 和 R5 如说明中所定义、 它们的对映体、非对映异构体和同系物，以及它们与药学上可接受的酸或碱的加成盐。
• US6875788B2
  申请人：——

  公开号：US6875788B2

  公开（公告）日：2005-04-05
• 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.