2-(4-fluorophenyl)-2-(1-methylpiperidin-4-yl)-1-[4-(4-naphthalen-1-ylbutyl)piperazin-1-yl]ethanone | 929268-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-fluorophenyl)-2-(1-methylpiperidin-4-yl)-1-[4-(4-naphthalen-1-ylbutyl)piperazin-1-yl]ethanone
• CAS: 929268-63-3
• 化学式: C₃₂H₄₀FN₃O
• 分子量: 501.688
• InChiKey: UFSLIQOPPIVNAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  26.79
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-2-(1-methylpiperidin-4-yl)-1-[4-(4-naphthalen-1-ylbutyl)piperazin-1-yl]ethanone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (+/-)-1-[2-(4-Fluorophenyl)-2-(1-methylpiperidin-4-yl)ethyl]-4-[4-(1-naphthyl)butyl]piperazine tri hydrochloride
  参考文献：
  名称：

  Novel piperazines: Potent melanocortin-4 receptor antagonists with anxiolytic-like activity

  摘要：

  In the present study, we found that a novel piperazine compound, 11a, showed a moderate affinity (IC50 = 333 nM) for the MC4 receptor. We developed the new type of piperazine compounds and found that mono-piperazine 11b exhibited a high-affinity (IC50 = 40.3 nM) for the MC4 receptor. We also found that a series of biphenyl analogues exhibited a high-affinity for the receptor, and in particular, compound 11j exhibited the highest affinity for the MC4 receptor with an IC50 value of 14.5 nM. Further-more, some of these compounds, when administered orally, significantly reversed the stress-induced anxiety-like behavior in rats. In this paper, we report the synthesis, structure-activity relationships, and oral activity of the novel mono-piperazines as MC4 receptor antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.019
• 作为产物：
  描述：

  (+/-)-[1-(tert-butoxycarbonyl)-4-hydroxypiperidin-4-yl](4-fluorophenyl)acetic acid 在 palladium dihydroxide 盐酸 、 sodium hydroxide 、 硫酸 、 氢气 、 potassium carbonate 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 83.5h， 生成 2-(4-fluorophenyl)-2-(1-methylpiperidin-4-yl)-1-[4-(4-naphthalen-1-ylbutyl)piperazin-1-yl]ethanone
  参考文献：
  名称：

  Novel piperazines: Potent melanocortin-4 receptor antagonists with anxiolytic-like activity

  摘要：

  In the present study, we found that a novel piperazine compound, 11a, showed a moderate affinity (IC50 = 333 nM) for the MC4 receptor. We developed the new type of piperazine compounds and found that mono-piperazine 11b exhibited a high-affinity (IC50 = 40.3 nM) for the MC4 receptor. We also found that a series of biphenyl analogues exhibited a high-affinity for the receptor, and in particular, compound 11j exhibited the highest affinity for the MC4 receptor with an IC50 value of 14.5 nM. Further-more, some of these compounds, when administered orally, significantly reversed the stress-induced anxiety-like behavior in rats. In this paper, we report the synthesis, structure-activity relationships, and oral activity of the novel mono-piperazines as MC4 receptor antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.019