1-[(1-Phenylpyrazol-4-yl)methyl]-4-(5-tricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaenyl)piperazine | 1428654-83-4

• 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-Phenylpyrazol-4-yl)methyl]-4-(5-tricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaenyl)piperazine
• 英文别名: 1-[(1-phenylpyrazol-4-yl)methyl]-4-(5-tricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaenyl)piperazine
• CAS: 1428654-83-4
• 化学式: C₃₀H₃₂N₄
• 分子量: 448.611
• InChiKey: VVPCRKVUSARVSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  24.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-苯基-1H-吡唑-4-甲醛 、 4-[2.2]paracyclophanylpiperazine 在 三乙酰氧基硼氢化钠 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以72%的产率得到1-[(1-Phenylpyrazol-4-yl)methyl]-4-(5-tricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaenyl)piperazine
  参考文献：
  名称：

  Discovery of dopamine D4 receptor antagonists with planar chirality

  摘要：

  Employing the D-4 selective phenylpiperazine 2 as a lead compound, planar chiral analogs with paracyclophane substructure were synthesized and evaluated for their ability to bind and activate dopamine receptors. The study revealed that the introduction of a [2.2]paracyclophane moiety is tolerated by dopamine receptors of the D-2 family. Subtype selectivity for D-4 and ligand efficacy depend on the absolute configuration of the test compounds. Whereas the achiral single-layered lead 2 and the double-layered paracyclophane (R)-3 showed partial agonist properties, the enantiomer (S)-3 behaved as a neutral antagonist. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.065

文献信息

• Discovery of dopamine D4 receptor antagonists with planar chirality
  作者：Fabrizio Sanna、Birgit Ortner、Harald Hübner、Stefan Löber、Nuska Tschammer、Peter Gmeiner

  DOI：10.1016/j.bmc.2013.01.065

  日期：2013.4

  Employing the D-4 selective phenylpiperazine 2 as a lead compound, planar chiral analogs with paracyclophane substructure were synthesized and evaluated for their ability to bind and activate dopamine receptors. The study revealed that the introduction of a [2.2]paracyclophane moiety is tolerated by dopamine receptors of the D-2 family. Subtype selectivity for D-4 and ligand efficacy depend on the absolute configuration of the test compounds. Whereas the achiral single-layered lead 2 and the double-layered paracyclophane (R)-3 showed partial agonist properties, the enantiomer (S)-3 behaved as a neutral antagonist. (C) 2013 Elsevier Ltd. All rights reserved.