1-(biphenyl-2-ylmethyl)-4-(2,4-dimethylphenyl)piperazine | 1430810-67-5

• 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-(biphenyl-2-ylmethyl)-4-(2,4-dimethylphenyl)piperazine
• 英文别名: 1-(Biphenyl-2-ylmethyl)-4-(2,4-dimethylphenyl)piperazine；1-(2,4-dimethylphenyl)-4-[(2-phenylphenyl)methyl]piperazine
• CAS: 1430810-67-5
• 化学式: C₂₅H₂₈N₂
• 分子量: 356.511
• InChiKey: OWIDBBBKDHVHLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  邻溴苯甲醛 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-(biphenyl-2-ylmethyl)-4-(2,4-dimethylphenyl)piperazine
  参考文献：
  名称：

  Discovery of aryl-biphenyl-2-ylmethylpiperazines as novel scaffolds for 5-HT7 ligands and role of the aromatic substituents in binding to the target receptor

  摘要：

  It has been reported that 5-HT7 receptors are promising targets of depression and neuropathic pain. 5-HT7 receptor antagonists have exhibited antidepressant-like profiles, while agonists have represented potential therapeutics for pain. In the course of our ongoing efforts to discover novel 5-HT7 modulators, we designed an arylpiperazine scaffold with a substituted biphenyl-2-ylmethyl group. A series of biphenyl-2-yl-arylpiperazinylmethanes were then prepared, which showed a broad spectrum of binding affinities to the 5-HT7 receptor depending upon the substituents attached to the biphenyl and aryl functionalities. Among those synthesized compounds, the compounds 1-24 and 1-26 showed the best binding affinities to the 5-HT7 receptor with K-i values of 43.0 and 46.0 nM, respectively. Structure-activity relationship study in conjunction with molecular docking study proposed that the 5-HT7 receptor might have two distinctive hydrophobic binding sites, one specific for aromatic 2-OCH3 substituents within the arylpiperazine and the other for biphenyl methoxy group. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.038

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。
• HYDRAZINO 1H-IMIDAZOQUINOLIN-4-AMINES AND CONJUGATES MADE THEREFROM
  申请人：Wightman Paul D.

  公开号：US20140286988A1

  公开（公告）日：2014-09-25

  1H-Imidazo[4,5-c]quinolin-4-amines substituted at the 1-position with a substituent bearing a hydrazinobenzamide or hydrazinonicotinamide, a salt thereof, or a protected hydrazinobenzamide or hydrazinonicotinamide and conjugates made from such compounds are disclosed. Pharmaceutical compositions containing the compound or the conjugate, methods of making a conjugate, and methods of use of the compounds or conjugates as immunomodulators for inducing cytokine biosynthesis in an animal and for vaccinating an animal are also disclosed.

  本发明涉及在1位取代了含有肼基苯甲酰胺或肼基烟酰胺的取代基，其盐或受保护的肼基苯甲酰胺或肼基烟酰胺的1H-咪唑并[4,5-c]喹啉-4-胺化合物及其共轭物。还公开了含有该化合物或共轭物的制药组合物，制备共轭物的方法以及将该化合物或共轭物用作免疫调节剂诱导动物细胞因子生物合成和动物疫苗接种的方法。
• 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。
• HETEROBIFUNCTIONAL LINKERS WITH POLYETHYLENE GLYCOL SEGMENTS AND IMMUNE RESPONSE MODIFIER CONJUGATES MADE THEREFROM
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US20140227317A1

  公开（公告）日：2014-08-14

  Conjugates of an immune response modifier, a linker, and an antigen are disclosed. The linker is represented by formula (I): wherein A is CH or N, p is in a range from 1 to 50, R″ is a bond or -alkylene-O—, R′ is alkylene that is optionally interrupted or terminated with one or more amide or ether groups, and E is an amine- or thiol-reactive group. Pharmaceutical compositions containing the compound or the conjugate, methods of making a conjugate, and methods of use of the compounds or conjugates as immunomodulators for inducing cytokine biosynthesis in an animal and for vaccinating an animal are also disclosed. An antigen modified by the linker is also disclosed.

  本文揭示了一种免疫应答调节剂、连接剂和抗原的共轭体。连接剂由式(I)表示：其中A为CH或N，p在1到50的范围内，R″为键或-烷基-O-，R′为烷基，可选地中断或终止于一个或多个酰胺或醚基团，E为胺基或硫醇反应基团。还揭示了含有该化合物或共轭体的制药组合物，制备共轭体的方法，以及将化合物或共轭体用作免疫调节剂在动物体内诱导细胞因子生物合成和预防动物的方法。还揭示了由连接剂修饰的抗原。
• Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US10723731B2

  公开（公告）日：2020-07-28

  Conjugates of an immune response modifier, a linker, and an antigen are disclosed. The linker is represented by formula: wherein A is CH or N, p is in a range from 1 to 50, R″ is a bond or -alkylene-O—, R′ is alkylene that is optionally interrupted or terminated with one or more amide or ether groups, and E is an amine- or thiol-reactive group. Pharmaceutical compositions containing the compound or the conjugate, methods of making a conjugate, and methods of use of the compounds or conjugates as immunomodulators for inducing cytokine biosynthesis in an animal and for vaccinating an animal are also disclosed. An antigen modified by the linker is also disclosed.

  本发明公开了一种免疫反应调节剂、一种连接体和一种抗原的共轭物。连接物由式表示： 其中A是CH或N，p在1至50的范围内，R″是键或-亚烷基-O-，R′是任选用一个或多个酰胺或醚基团间断或终止的亚烷基，E是胺或硫醇反应基团。还公开了含有化合物或共轭物的药物组合物、共轭物的制造方法以及化合物或共轭物作为免疫调节剂用于诱导动物体内细胞因子的生物合成和为动物接种疫苗的使用方法。还公开了经连接体修饰的抗原。