1-(4-(3-bromopropoxy)benzyl)piperidine | 913380-87-7

• 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-(4-(3-bromopropoxy)benzyl)piperidine
• 英文别名: 1-[[4-(3-Bromopropoxy)phenyl]methyl]piperidine
• CAS: 913380-87-7
• 化学式: C₁₅H₂₂BrNO
• 分子量: 312.25
• InChiKey: MOAARFBVMPLBIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-二氨基喹喔啉 、 1-(4-(3-bromopropoxy)benzyl)piperidine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2,3-diamino-N2-(3-(4-(piperidin-1-ylmethyl)phenoxy)propyl)quinoxaline
  参考文献：
  名称：

  Searching for the Multi-Target-Directed Ligands against Alzheimer’s disease: Discovery of quinoxaline-based hybrid compounds with AChE, H3R and BACE 1 inhibitory activities

  摘要：

  A novel series of quinoxaline derivatives, as Multi-Target-Directed Ligands (MTDLs) for AD treatment, were designed by lending the core structural elements required for H3R antagonists and hybridizing BACE 1 inhibitor 1 with AChE inhibitor BYYT-25. A virtual database consisting of quinoxaline derivatives was first screened on a pharmacophore model of BACE 1 inhibitors, and then filtered by a molecular docking model of AChE. Seventeen quinoxaline derivatives with high score values were picked out, synthesized and evaluated for their biological activities. Compound 11a, the most effective MTDL, showed the potent activity to H3R/AChE/BACE 1 (H3R antagonism, IC50 = 280.0 +/- 98.0 nM; H3R inverse agonism, IC50 = 189.3 +/- 95.7 nM; AChE, IC50 = 483 +/- 5 nM; BACE 1, 46.64 +/- 2.55% inhibitory rate at 20 mu M) and high selectivity over H1R/H2R/H4R. Furthermore, the protein binding patterns between 11a and AChE/BACE 1 showed that it makes several essential interactions with the enzymes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.061
• 作为产物：
  描述：

  4-(哌啶-1-基甲基)苯酚 、 1,3-二溴丙烷 在 四丁基溴化铵 、 sodium hydroxide 作用下， 反应 4.0h， 生成 1-(4-(3-bromopropoxy)benzyl)piperidine
  参考文献：
  名称：

  Searching for the Multi-Target-Directed Ligands against Alzheimer’s disease: Discovery of quinoxaline-based hybrid compounds with AChE, H3R and BACE 1 inhibitory activities

  摘要：

  A novel series of quinoxaline derivatives, as Multi-Target-Directed Ligands (MTDLs) for AD treatment, were designed by lending the core structural elements required for H3R antagonists and hybridizing BACE 1 inhibitor 1 with AChE inhibitor BYYT-25. A virtual database consisting of quinoxaline derivatives was first screened on a pharmacophore model of BACE 1 inhibitors, and then filtered by a molecular docking model of AChE. Seventeen quinoxaline derivatives with high score values were picked out, synthesized and evaluated for their biological activities. Compound 11a, the most effective MTDL, showed the potent activity to H3R/AChE/BACE 1 (H3R antagonism, IC50 = 280.0 +/- 98.0 nM; H3R inverse agonism, IC50 = 189.3 +/- 95.7 nM; AChE, IC50 = 483 +/- 5 nM; BACE 1, 46.64 +/- 2.55% inhibitory rate at 20 mu M) and high selectivity over H1R/H2R/H4R. Furthermore, the protein binding patterns between 11a and AChE/BACE 1 showed that it makes several essential interactions with the enzymes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.061

文献信息

• [EN] MULTIPLE D2 A(NTA)GONISTS/H3 ANTAGONISTS FOR TREATMENT OF CNS-RELATED DISORDERS<br/>[FR] MULTIPLES A(NTA)GONISTES DE D2/ANTAGONISTES DE H3 POUR LE TRAITEMENT DE TROUBLES ASSOCIÉS AU SNC
  申请人：AAPA B V

  公开号：WO2015069110A1

  公开（公告）日：2015-05-14

  The present invention relates to compounds compound according to Formula (III); and pharmaceutically acceptable salts, hydrates and solvates thereof. These compounds have D2receptor antagonist/(partial) agonist effects and H3antagonistic effects, pharmaceutical compositions thereof, and methods of using them for application in the prophylaxis or treatment of CNS disorders.

  本发明涉及按照式（III）的化合物；以及其药学上可接受的盐、水合物和溶剂合物。这些化合物具有D2受体拮抗/(部分)激动剂效应和H3拮抗效应，以及其药物组合物，以及将其用于预防或治疗中枢神经系统疾病的方法。
• Design, synthesis and evaluation of galanthamine derivatives as acetylcholinesterase inhibitors
  作者：Ping Jia、Rong Sheng、Jing Zhang、Liang Fang、Qiaojun He、Bo Yang、Yongzhou Hu

  DOI：10.1016/j.ejmech.2008.04.018

  日期：2009.2

  A new series of galanthamine derivatives have been designed, synthesized and evaluated as acetylcholinesterase inhibitors. All of the new compounds prepared showed high AChE inhibitory activities, with compound 3e that has an N-hexyl-benzyl piperidine substituent on the nitrogen atom reaching the best inhibitory activity for AChE (IC50 = 5.62 nM). The docking study performed with AutoDock demonstrated that 3e was nicely accommodated by AChE. (c) 2008 Elsevier Masson SAS. All rights reserved.
• Searching for the Multi-Target-Directed Ligands against Alzheimer’s disease: Discovery of quinoxaline-based hybrid compounds with AChE, H3R and BACE 1 inhibitory activities
  作者：Wenhai Huang、Li Tang、Ying Shi、Shufang Huang、Lei Xu、Rong Sheng、Peng Wu、Jia Li、Naiming Zhou、Yongzhou Hu

  DOI：10.1016/j.bmc.2011.09.061

  日期：2011.12

  A novel series of quinoxaline derivatives, as Multi-Target-Directed Ligands (MTDLs) for AD treatment, were designed by lending the core structural elements required for H3R antagonists and hybridizing BACE 1 inhibitor 1 with AChE inhibitor BYYT-25. A virtual database consisting of quinoxaline derivatives was first screened on a pharmacophore model of BACE 1 inhibitors, and then filtered by a molecular docking model of AChE. Seventeen quinoxaline derivatives with high score values were picked out, synthesized and evaluated for their biological activities. Compound 11a, the most effective MTDL, showed the potent activity to H3R/AChE/BACE 1 (H3R antagonism, IC50 = 280.0 +/- 98.0 nM; H3R inverse agonism, IC50 = 189.3 +/- 95.7 nM; AChE, IC50 = 483 +/- 5 nM; BACE 1, 46.64 +/- 2.55% inhibitory rate at 20 mu M) and high selectivity over H1R/H2R/H4R. Furthermore, the protein binding patterns between 11a and AChE/BACE 1 showed that it makes several essential interactions with the enzymes. (C) 2011 Elsevier Ltd. All rights reserved.