2-(cyclohexylphenyl)methyl-1H-benzimidazole | 862898-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(cyclohexylphenyl)methyl-1H-benzimidazole
• 英文别名: S27847；1H-Benzimidazole, 2-(cyclohexylphenylmethyl)-；2-[cyclohexyl(phenyl)methyl]-1H-benzimidazole
• CAS: 862898-23-5
• 化学式: C₂₀H₂₂N₂
• 分子量: 290.408
• InChiKey: QIUUASDUULWILV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  α-苯基环戊基乙酸 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-(cyclohexylphenyl)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

文献信息

• Cycloalkyl inhibitors of potassium channel function
  申请人：——

  公开号：US20040072880A1

  公开（公告）日：2004-04-15

  Novel cycloalkyl compounds useful as inhibitors of potassium channel function (especially inhibitors of the K v 1 subfamily of voltage gated K + channels, especially inhibitors K v 1.5 which has been linked to the ultra-rapidly activating delayed rectifier K + current I Kur ), methods of using such compounds in the prevention and treatment of arrhythmia and I Kur -associated conditions, and pharmaceutical compositions containing such compounds.

  新型环烷基化合物可用作钾通道功能抑制剂（特别是Kv1亚家族电压门控K+通道的抑制剂，特别是抑制与超快速激活延迟整流K+电流IKur相关的Kv1.5），使用这些化合物预防和治疗心律失常和IKur相关疾病的方法，以及含有这些化合物的制药组合物。
• CYCLOALKYL INHIBITORS OF POTASSIUM CHANNEL FUNCTION
  申请人：Lloyd John

  公开号：US20070142333A1

  公开（公告）日：2007-06-21

  Novel cycloalkyl compounds useful as inhibitors of potassium channel function (especially inhibitors of the K v 1 subfamily of voltage gated K + channels, especially inhibitors K v 1.5 which has been linked to the ultra-rapidly activating delayed rectifier K + current I Kur ), methods of using such compounds in the prevention and treatment of arrhythmia and I Kur -associated conditions, and pharmaceutical compositions containing such compounds.

  新型环烷基化合物可作为钾通道功能抑制剂使用（特别是钾离子电压门控K+通道的Kv1亚家族的抑制剂，特别是与超快速激活延迟整流K+电流IKur相关的Kv1.5抑制剂），使用这种化合物预防和治疗心律失常和IKur相关疾病的方法，以及含有这种化合物的药物组合物。
• 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.
• 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.
• US7202253B2
  申请人：——

  公开号：US7202253B2

  公开（公告）日：2007-04-10