3-(1-benzylpiperidin-4-yl)-1-(2,3-dihydrobenzo<1,4>dioxin-6-yl)-prop-2-en-1-one | 163726-68-9

• 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: 3-(1-benzylpiperidin-4-yl)-1-(2,3-dihydrobenzo<1,4>dioxin-6-yl)-prop-2-en-1-one
• 英文别名: (E)-3-(1-benzylpiperidin-4-yl)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-en-1-one
• CAS: 163726-68-9
• 化学式: C₂₃H₂₅NO₃
• 分子量: 363.456
• InChiKey: JOMRXGKBFCTTDY-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1-benzylpiperidin-4-yl)-1-(2,3-dihydrobenzo<1,4>dioxin-6-yl)-prop-2-en-1-one 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 3-(1-benzylpiperidin-4-yl)-1-(2,3-dihydrobenzo<1,4>dioxin-6-yl)-propan-1-one
  参考文献：
  名称：

  Design and Synthesis of 1-Heteroaryl-3-(1-benzyl-4-piperidinyl)propan-1-one Derivatives as Potent, Selective Acetylcholinesterase Inhibitors

  摘要：

  Herein is described the synthesis and structure-activity relationship of a novel series of aromatic and heteroaromatic 3-(1-benzyl-4-piperidinyl)propan-1-one derivatives that display potent and selective inhibition of the enzyme acetylcholinesterase (AChE). 1-(2-Methyl-6-benzothiazolyl)-3-(N-benzyl-4-piperidinyl)propan-1-one hydrochloride, 6d, is one of the most active compounds within this series exhibiting an IC50 for the inhibition of the AChE enzyme equal to 6.8 nM. Compound 6d has shown a dose-dependent elevation of total acetylcholine (ACh) levels in the mouse forebrain with an oral ED(50) = 9.8 mg/kg. In addition, in vivo microdialysis experiments in the rat demonstrate that 6d increases extracellular ACh (100% over basal) 1-3 h postdose with an oral ED(50) = 4.8 mg/kg.

  DOI：

  10.1021/jm00007a005
• 作为产物：
  描述：

  1-苄基-4-哌啶甲醛 在 盐酸 、 正丁基锂 作用下， 生成 3-(1-benzylpiperidin-4-yl)-1-(2,3-dihydrobenzo<1,4>dioxin-6-yl)-prop-2-en-1-one
  参考文献：
  名称：

  Quaternary Salts of E2020 Analogues as Acetylcholinesterase Inhibitors for the Reversal of Neuromuscular Block

  摘要：

  A series benzylpiperidinium and benzylpyridinium quaternary salts have been synthesised and tested for inhibition of acetylcholinesterase and reversal of neuromuscular block induced by vecuronium. Several potent reversal agents have been identified and their haemodynamic effects measured. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00482-1

文献信息

• Quaternary Salts of E2020 Analogues as Acetylcholinesterase Inhibitors for the Reversal of Neuromuscular Block
  作者：John K Clark、Phill Cowley、Alan W Muir、Ronald Palin、Eleanor Pow、Alan B Prosser、Robert Taylor、Ming-Qiang Zhang

  DOI：10.1016/s0960-894x(02)00482-1

  日期：2002.9

  A series benzylpiperidinium and benzylpyridinium quaternary salts have been synthesised and tested for inhibition of acetylcholinesterase and reversal of neuromuscular block induced by vecuronium. Several potent reversal agents have been identified and their haemodynamic effects measured. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Design and Synthesis of 1-Heteroaryl-3-(1-benzyl-4-piperidinyl)propan-1-one Derivatives as Potent, Selective Acetylcholinesterase Inhibitors
  作者：Arthur A. Nagel、Dane R. Liston、Stanley Jung、Melissa Mahar、Lawrence A. Vincent、Douglas Chapin、Yuhpyng L. Chen、Sean Hubbard、Jeffrey L. Ives

  DOI：10.1021/jm00007a005

  日期：1995.3

  Herein is described the synthesis and structure-activity relationship of a novel series of aromatic and heteroaromatic 3-(1-benzyl-4-piperidinyl)propan-1-one derivatives that display potent and selective inhibition of the enzyme acetylcholinesterase (AChE). 1-(2-Methyl-6-benzothiazolyl)-3-(N-benzyl-4-piperidinyl)propan-1-one hydrochloride, 6d, is one of the most active compounds within this series exhibiting an IC50 for the inhibition of the AChE enzyme equal to 6.8 nM. Compound 6d has shown a dose-dependent elevation of total acetylcholine (ACh) levels in the mouse forebrain with an oral ED(50) = 9.8 mg/kg. In addition, in vivo microdialysis experiments in the rat demonstrate that 6d increases extracellular ACh (100% over basal) 1-3 h postdose with an oral ED(50) = 4.8 mg/kg.