(3-{[2-(3-Hydroxy-phenoxy)-ethylamino]-methyl}-phenyl)-piperidin-1-yl-methanone | 748773-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-{[2-(3-Hydroxy-phenoxy)-ethylamino]-methyl}-phenyl)-piperidin-1-yl-methanone
• 英文别名: [3-[[2-(3-hydroxyphenoxy)ethylamino]methyl]phenyl]-piperidin-1-ylmethanone
• CAS: 748773-13-9
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: JFCSQOSJIKLTJG-UHFFFAOYSA-N

物化性质

• 沸点：
  572.2±45.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-碘代丙烷 、 (3-{[2-(3-Hydroxy-phenoxy)-ethylamino]-methyl}-phenyl)-piperidin-1-yl-methanone 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3-{[2-(3-isopropoxy-phenoxy)-ethylamino]-methyl}-phenyl)-piperidin-1-yl-methanone
  参考文献：
  名称：

  Inhibitors of the glycine transporter type-2 (GlyT-2): synthesis and biological activity of benzoylpiperidine derivatives

  摘要：

  A series of benzoylpiperidine analogs related to 4a was prepared, and their ability to inhibit the uptake of [C-14]-glycine in COS7 cells transfected with human glycine transporter type-2 (GlyT-2) was evaluated. Small structural changes to the benzoylpiperidine region of the molecule led to a significant decrease in GlyT-2 inhibitory activity. In contrast, the distal aryl ring was more tolerant to functional group modifications and could accommodate a variety of substitutes at the C-2 or C-3 positions. Comparable activities to 4a were obtained by replacing the anilino nitrogen with an ether linkage 27 or by exchanging the isopropoxy ether moiety with an isopropyl amino group 15. A distinct preference for a 2-carbon tether (n = 1) was observed relative to the corresponding 3-carbon homolog (n = 2). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.044
• 作为产物：
  描述：

  3-羧基苯甲醛 在 sodium hydroxide 、 三乙酰氧基硼氢化钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (3-{[2-(3-Hydroxy-phenoxy)-ethylamino]-methyl}-phenyl)-piperidin-1-yl-methanone
  参考文献：
  名称：

  Inhibitors of the glycine transporter type-2 (GlyT-2): synthesis and biological activity of benzoylpiperidine derivatives

  摘要：

  A series of benzoylpiperidine analogs related to 4a was prepared, and their ability to inhibit the uptake of [C-14]-glycine in COS7 cells transfected with human glycine transporter type-2 (GlyT-2) was evaluated. Small structural changes to the benzoylpiperidine region of the molecule led to a significant decrease in GlyT-2 inhibitory activity. In contrast, the distal aryl ring was more tolerant to functional group modifications and could accommodate a variety of substitutes at the C-2 or C-3 positions. Comparable activities to 4a were obtained by replacing the anilino nitrogen with an ether linkage 27 or by exchanging the isopropoxy ether moiety with an isopropyl amino group 15. A distinct preference for a 2-carbon tether (n = 1) was observed relative to the corresponding 3-carbon homolog (n = 2). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.044

文献信息

• Aryl piperidine amides
  申请人：Huang Q. Charles

  公开号：US20050049239A1

  公开（公告）日：2005-03-03

  The invention provides novel GlyT2 inhibiting compounds useful in modulating, treating, or preventing: anxiolytic disorders; a condition requiring treatment of injured mammalian nerve tissue; a condition amenable to treatment through administration of a neurotrophic factor; a neurological disorder; or obesity; an obesity-related disorder.

  该发明提供了新颖的GlyT2抑制化合物，可用于调节、治疗或预防：焦虑症；需要治疗受伤哺乳动物神经组织的状况；适合通过神经营养因子管理治疗的状况；神经系统紊乱；或肥胖症；与肥胖相关的疾病。