(1-(cyclohexylmethyl)piperidin-4-yl)methanamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1-(cyclohexylmethyl)piperidin-4-yl)methanamine
• 英文别名: [1-(cyclohexylmethyl)-4-piperidyl]methanamine；[1-(Cyclohexylmethyl)piperidin-4-yl]methanamine
• 化学式: C₁₃H₂₆N₂
• 分子量: 210.363
• InChiKey: BVSQSPAHHLJKMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-(cyclohexylmethyl)piperidin-4-yl)methanamine 在 双氧水 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 4-amino-5-iodo-N-[[1-(cyclohexylmethyl)-4-piperidyl]methyl]-2-methoxybenzamide
  参考文献：
  名称：

  Synthesis and evaluation of novel serotonin 4 receptor radiotracers for single photon emission computed tomography

  摘要：

  Despite its implication in several physiological and pathological processes the serotonin subtype-4 receptor (5-HT4R) has seen limited effort for the development of radiolabeling agent especially concerning single photon emission computed tomography (SPECT). Bearing an ester function, the available ligands are rapidly susceptible to hydrolysis which limits their use in vivo. In this study the synthesis of iodinated benzamide and ketone analogs were described. Their affinity for the 5-HT4R and their lipophilicity were evaluated and the most promising derivatives were evaluated ex vivo for their binding to the receptor and for their ability to displace the reference ligand [I-125]-SB207710. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.059
• 作为产物：
  描述：

  哌啶-4-甲酰胺 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 28.0h， 生成 (1-(cyclohexylmethyl)piperidin-4-yl)methanamine
  参考文献：
  名称：

  Synthesis and evaluation of novel serotonin 4 receptor radiotracers for single photon emission computed tomography

  摘要：

  Despite its implication in several physiological and pathological processes the serotonin subtype-4 receptor (5-HT4R) has seen limited effort for the development of radiolabeling agent especially concerning single photon emission computed tomography (SPECT). Bearing an ester function, the available ligands are rapidly susceptible to hydrolysis which limits their use in vivo. In this study the synthesis of iodinated benzamide and ketone analogs were described. Their affinity for the 5-HT4R and their lipophilicity were evaluated and the most promising derivatives were evaluated ex vivo for their binding to the receptor and for their ability to displace the reference ligand [I-125]-SB207710. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.059

文献信息

• Structure-based exploration and pharmacological evaluation of N-substituted piperidin-4-yl-methanamine CXCR4 chemokine receptor antagonists
  作者：I. Adlere、S. Sun、A. Zarca、L. Roumen、M. Gozelle、C. Perpiñá Viciano、B. Caspar、M. Arimont、J.P. Bebelman、S.J. Briddon、C. Hoffmann、S.J. Hill、M.J. Smit、H.F. Vischer、M. Wijtmans、C. de Graaf、I.J.P. de Esch、R. Leurs

  DOI：10.1016/j.ejmech.2018.10.060

  日期：2019.1

  Using the available structural information of the chemokine receptor CXCR4, we present hit finding and hit exploration studies that make use of virtual fragment screening, design, synthesis and structure-activity relationship (SAR) studies. Fragment 2 was identified as virtual screening hit and used as a starting point for the exploration of 31 N-substituted piperidin-4-yl-methanamine derivatives to

  利用趋化因子受体CXCR4的可用结构信息，我们提出了利用虚拟片段筛选，设计，合成和结构-活性关系（SAR）研究的命中发现和命中探索研究。片段2被鉴定为虚拟筛选命中点，并被用作探索31种N-取代的哌啶-4-基-甲胺衍生物的起点，以研究和改善与CXCR4结合位点的相互作用。另外，细微的结构配体变化导致与CXCR4发生明显的相互作用，导致CXCL12结合的完全或部分移位以及竞争性和/或非竞争性拮抗作用。三维定量结构-活性关系（3D-QSAR）和结合模型研究用于确定重要的疏水相互作用，这些相互作用决定了结合亲和力并表明了关键的配体-受体相互作用。
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  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0604494B1

  公开（公告）日：1999-07-28
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