1-(4-chlorophenyl)-4-(4-(4-fluorophenyl)butyl)piperazine | 1359849-90-3

• 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-(4-chlorophenyl)-4-(4-(4-fluorophenyl)butyl)piperazine
• 英文别名: 1-(4-Chlorophenyl)-4-[4-(4-fluorophenyl)butyl]piperazine
• CAS: 1359849-90-3
• 化学式: C₂₀H₂₄ClFN₂
• 分子量: 346.875
• InChiKey: ARWONURFSGKTJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氟苯基溴化镁 在 CuLi₂O₄ 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 丙酮 为溶剂， 反应 38.0h， 生成 1-(4-chlorophenyl)-4-(4-(4-fluorophenyl)butyl)piperazine
  参考文献：
  名称：

  Multi-receptor drug design: Haloperidol as a scaffold for the design and synthesis of atypical antipsychotic agents

  摘要：

  Using haloperidol as a scaffold, new agents were designed to investigate the structural contributions of various groups to binding at CNS receptors associated with atypical antipsychotic pharmacology. It is clear that each pharmacophoric group, the butyrophenone, the piperidine and the 4-chlorophenyl moieties contributes to changes in binding to the receptors of interest. This strategy has resulted in the identification of several new agents, compounds 16, 18, 19, 23, 24 and 25, with binding profiles which satisfy our stated criteria for agents to act as potential atypical antipsychotics. This research demonstrates that haloperidol can serve as a useful lead in the identification and design of new agents that target multiple receptors associated with antipsychotic pharmacology. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.12.019

文献信息

• Identification of agents displaying functional activation of dopamine D2 and D4 receptors
  申请人：Florida A&M University

  公开号：US11129831B2

  公开（公告）日：2021-09-28

  A method of treating psychosis, and the underlying antipsychotic formulation. The method includes administering a therapeutically effective amount of synthetic agents that selectively recruit β-arrestin to D2 receptors and have little-to-no binding to culprit receptors associated with weight gain and Type II diabetes. The synthetic agents can include SYA16263 and SYA16264, and/or derivatives or analogs thereof. The 1-(pyridin-2-yl)piperazine moiety was found to play a significant role in recruiting β-arrestin to D2 receptors. In other embodiments, the current invention relates to synthetic agents that are selective of D4 receptors for treatment of psychosis and erectile dysfunction. The synthetic agents can include SYA27287 and/or derivatives or analogs thereof. In all embodiments, extrapyramidal side effects are eliminated or minimized.

  一种治疗精神病的方法和基础抗精神病制剂。该方法包括施用治疗有效量的合成制剂，这些制剂可选择性地将β-arrestin募集到D2受体，并且几乎不与与体重增加和II型糖尿病相关的罪魁祸首受体结合。合成制剂可包括 SYA16263 和 SYA16264 和/或其衍生物或类似物。研究发现，1-(吡啶-2-基)哌嗪分子在将β-阿司匹林募集到 D2 受体上发挥了重要作用。在其他实施方案中，本发明涉及对 D4 受体具有选择性的合成制剂，用于治疗精神病和勃起功能障碍。合成制剂可包括 SYA27287 和/或其衍生物或类似物。在所有实施方案中，锥体外系副作用均被消除或减至最小。
• IDENTIFICATION OF AGENTS DISPLAYING FUNCTIONAL ACTIVATION OF DOPAMINE D2 AND D4 RECEPTORS
  申请人：Florida A&M University

  公开号：US20210401838A1

  公开（公告）日：2021-12-30

  A method of treating psychosis, and the underlying antipsychotic formulation. The method includes administering a therapeutically effective amount of synthetic agents that selectively recruit β-arrestin to D2 receptors and have little-to-no binding to culprit receptors associated with weight gain and Type II diabetes. The synthetic agents can include SYA16263 and SYA16264, and/or derivatives or analogs thereof. The 1-(pyridin-2-yl)piperazine moiety was found to play a significant role in recruiting β-arrestin to D2 receptors. In other embodiments, the current invention relates to synthetic agents that are selective of D4 receptors for treatment of psychosis and erectile dysfunction. The synthetic agents can include SYA27287 and/or derivatives or analogs thereof. In all embodiments, extrapyramidal side effects are eliminated or minimized.
• Multi-receptor drug design: Haloperidol as a scaffold for the design and synthesis of atypical antipsychotic agents
  作者：Kwakye Peprah、Xue Y. Zhu、Suresh V.K. Eyunni、Vincent Setola、Bryan L. Roth、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2011.12.019

  日期：2012.2

  Using haloperidol as a scaffold, new agents were designed to investigate the structural contributions of various groups to binding at CNS receptors associated with atypical antipsychotic pharmacology. It is clear that each pharmacophoric group, the butyrophenone, the piperidine and the 4-chlorophenyl moieties contributes to changes in binding to the receptors of interest. This strategy has resulted in the identification of several new agents, compounds 16, 18, 19, 23, 24 and 25, with binding profiles which satisfy our stated criteria for agents to act as potential atypical antipsychotics. This research demonstrates that haloperidol can serve as a useful lead in the identification and design of new agents that target multiple receptors associated with antipsychotic pharmacology. Published by Elsevier Ltd.