1-(4-fluorophenyl)-2-{4-[4-(1-naphthyl)butyl]piperazin-1-yl}ethanone | 932028-02-9

• 英文名称: 1-(4-fluorophenyl)-2-{4-[4-(1-naphthyl)butyl]piperazin-1-yl}ethanone
• CAS: 932028-02-9
• 化学式: C₂₆H₂₉FN₂O
• 分子量: 404.527
• InChiKey: VRGCRRIMBBQWOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  23.55
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-2-{4-[4-(1-naphthyl)butyl]piperazin-1-yl}ethanone 在 sodium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 7.0h， 生成 tert-butyl 4-(1-(4-fluorophenyl)-2-{4-[4-(1-naphthyl)butyl]piperazin-1-yl}ethyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Structure–activity relationships of novel piperazines as antagonists for the melanocortin-4 receptor

  摘要：

  During the investigation of antagonists for the MC4 receptor, we found that 10ab having a naphthyl group showed almost the same binding affinity for the MC4 receptor as that of the lead compound I with a benzoyl group. We also developed a new type of compounds.. namely, bis-piperazines, and found that the bis-piperazines 10 exhibited a high affinity for the MC4 receptor. In particular, (-)-10bg exhibited the highest affinity for the MC4 receptor with an IC50 value of 8.13 nM. In this paper, we present the design, synthesis, and structure-activity relationships of the novel bis-piperazines as MC4 receptor antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.039
• 作为产物：
  描述：

  2-氯代-4'-氟苯乙酮 、 1-(4-naphthalen-1-yl-butyl)piperazine dihydrochloride 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以100%的产率得到1-(4-fluorophenyl)-2-{4-[4-(1-naphthyl)butyl]piperazin-1-yl}ethanone
  参考文献：
  名称：

  Structure–activity relationships of novel piperazines as antagonists for the melanocortin-4 receptor

  摘要：

  During the investigation of antagonists for the MC4 receptor, we found that 10ab having a naphthyl group showed almost the same binding affinity for the MC4 receptor as that of the lead compound I with a benzoyl group. We also developed a new type of compounds.. namely, bis-piperazines, and found that the bis-piperazines 10 exhibited a high affinity for the MC4 receptor. In particular, (-)-10bg exhibited the highest affinity for the MC4 receptor with an IC50 value of 8.13 nM. In this paper, we present the design, synthesis, and structure-activity relationships of the novel bis-piperazines as MC4 receptor antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.039