1-[4-(3-Piperidin-1-ylpropoxy)phenyl]cyclohexan-1-ol | 1334335-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[4-(3-Piperidin-1-ylpropoxy)phenyl]cyclohexan-1-ol
• 英文别名: 1-[4-(3-piperidin-1-ylpropoxy)phenyl]cyclohexan-1-ol
• CAS: 1334335-30-6
• 化学式: C₂₀H₃₁NO₂
• 分子量: 317.472
• InChiKey: HGGUHLCAFDTKKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[4-(3-Piperidin-1-ylpropoxy)phenyl]cyclohexan-1-ol 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 1-[3-[4-(Cyclohexen-1-yl)phenoxy]propyl]piperidine
  参考文献：
  名称：

  Novel and highly potent histamine H3 receptor ligands. Part 1: withdrawing of hERG activity

  摘要：

  Pre-clinical investigation of some aryl-piperidinyl ether histamine H3 receptor antagonists revealed a strong hERG binding. To overcome this issue, we have developed a QSAR model specially dedicated to H3 receptor ligands. This model was designed to be directly applicable in medicinal chemistry with no need of molecular modeling. The resulting recursive partitioning trees are robust (80-85% accuracy), but also simple and comprehensible. A novel promising lead emerged from our work and the structure-activity relationships are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.006
• 作为产物：
  描述：

  1-bromo-4-(3-piperidin-1-yl-propoxy)benzene 、 环己酮 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 1-[4-(3-Piperidin-1-ylpropoxy)phenyl]cyclohexan-1-ol
  参考文献：
  名称：

  Novel and highly potent histamine H3 receptor ligands. Part 1: withdrawing of hERG activity

  摘要：

  Pre-clinical investigation of some aryl-piperidinyl ether histamine H3 receptor antagonists revealed a strong hERG binding. To overcome this issue, we have developed a QSAR model specially dedicated to H3 receptor ligands. This model was designed to be directly applicable in medicinal chemistry with no need of molecular modeling. The resulting recursive partitioning trees are robust (80-85% accuracy), but also simple and comprehensible. A novel promising lead emerged from our work and the structure-activity relationships are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.006

文献信息

• Novel and highly potent histamine H3 receptor ligands. Part 1: withdrawing of hERG activity
  作者：Nicolas Levoin、Olivier Labeeuw、Thierry Calmels、Olivia Poupardin-Olivier、Isabelle Berrebi-Bertrand、Jeanne-Marie Lecomte、Jean-Charles Schwartz、Marc Capet

  DOI：10.1016/j.bmcl.2011.07.006

  日期：2011.9

  Pre-clinical investigation of some aryl-piperidinyl ether histamine H3 receptor antagonists revealed a strong hERG binding. To overcome this issue, we have developed a QSAR model specially dedicated to H3 receptor ligands. This model was designed to be directly applicable in medicinal chemistry with no need of molecular modeling. The resulting recursive partitioning trees are robust (80-85% accuracy), but also simple and comprehensible. A novel promising lead emerged from our work and the structure-activity relationships are presented. (C) 2011 Elsevier Ltd. All rights reserved.
• Novel and highly potent histamine H3 receptor ligands. Part 3: An alcohol function to improve the pharmacokinetic profile
  作者：Olivier Labeeuw、Nicolas Levoin、Olivia Poupardin-Olivier、Thierry Calmels、Xavier Ligneau、Isabelle Berrebi-Bertrand、Philippe Robert、Jeanne-Marie Lecomte、Jean-Charles Schwartz、Marc Capet

  DOI：10.1016/j.bmcl.2013.02.118

  日期：2013.5

  Synthesis and biological evaluation of potent histamine H-3 receptor antagonists incorporating a hydroxyl function are described. Compounds in this series exhibited nanomolar binding affinities for human receptor, illustrating a new possible component for the H-3 pharmacophore. As demonstrated with compound BP1.4160 (cyclohexanol 19), the introduction of an alcohol function counter-intuitively allowed to reach high in vivo efficiency and favorable pharmacokinetic profile with reduced half-life. (C) 2013 Elsevier Ltd. All rights reserved.