1-([1,1'-biphenyl]-3-ylmethyl)-4-(2,4-dimethylphenyl)piperazine | 1442087-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-([1,1'-biphenyl]-3-ylmethyl)-4-(2,4-dimethylphenyl)piperazine
• 英文别名: 1-(biphenyl-3-ylmethyl)-4-(2,4-dimethylphenyl)piperazine；1-(2,4-dimethylphenyl)-4-[(3-phenylphenyl)methyl]piperazine
• CAS: 1442087-52-6
• 化学式: C₂₅H₂₈N₂
• 分子量: 356.511
• InChiKey: ZTEIXJFQKCQRGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 1-([1,1'-biphenyl]-3-ylmethyl)-4-(2,4-dimethylphenyl)piperazine
  参考文献：
  名称：

  Aryl Biphenyl-3-ylmethylpiperazines as 5-HT₇Receptor Antagonists

  摘要：

  AbstractThe 5‐HT7 receptor (5‐HT7R) is a promising therapeutic target for the treatment of depression and neuropathic pain. The 5‐HT7R antagonist SB‐269970 exhibited antidepressant‐like activity, whereas systemic administration of the 5‐HT7R agonist AS‐19 significantly inhibited mechanical hypersensitivity and thermal hyperalgesia. In our efforts to discover selective 5‐HT7R antagonists or agonists, aryl biphenyl‐3‐ylmethylpiperazines were designed, synthesized, and biologically evaluated against the 5‐HT7R. Among the synthesized compounds, 1‐([2′‐methoxy‐(1,1′‐biphenyl)‐3‐yl]methyl)‐4‐(2‐methoxyphenyl)piperazine (28) was the best binder to the 5‐HT7R (pKi=7.83), and its antagonistic property was confirmed by functional assays. The selectivity profile of compound 28 was also recorded for the 5‐HT7R over other serotonin receptor subtypes, such as 5‐HT1R, 5‐HT2R, 5‐HT3R, and 5‐HT6R. In a molecular modeling study, the 2‐methoxyphenyl moiety attached to the piperazine ring of compound 28 was proposed to be essential for the antagonistic function.

  DOI：

  10.1002/cmdc.201300240

文献信息

• BIPHENYL DERIVATIVES, PHARMACEUTICAL COMPOSITION COMPRISING THE SAME, AND PREPARATION METHOD THEREOF
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20140228568A1

  公开（公告）日：2014-08-14

  Provided are biphenyl derivatives exhibiting activity towards central nervous system diseases by acting on the 5-HT 7 receptor, pharmaceutically acceptable salts thereof, a method for preparing the compounds and pharmaceutical compositions including the compounds as an active ingredient.

  提供了对中枢神经系统疾病具有作用的二苯基衍生物，通过作用于5-HT7受体，其药学上可接受的盐，制备该化合物的方法以及包括该化合物作为活性成分的制药组合物。
• Biphenyl derivatives, pharmaceutical composition comprising the same, and preparation method thereof
  申请人：Korea Institute of Science and Technology

  公开号：US08883796B2

  公开（公告）日：2014-11-11

  Provided are biphenyl derivatives exhibiting activity towards central nervous system diseases by acting on the 5-HT7 receptor, pharmaceutically acceptable salts thereof, a method for preparing the compounds and pharmaceutical compositions including the compounds as an active ingredient.

  提供了对中枢神经系统疾病具有活性的双苯衍生物，通过作用于5-HT7受体，其药学上可接受的盐，制备这些化合物的方法以及包括这些化合物作为活性成分的制药组合物。
• US8883796B2
  申请人：——

  公开号：US8883796B2

  公开（公告）日：2014-11-11