3-(1-benzylpiperidin-4-yl)-3-hydroxy-1-(2-methylbenzothiazol-6-yl)propan-1-one

• 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)-3-hydroxy-1-(2-methylbenzothiazol-6-yl)propan-1-one
• 英文别名: 3-(1-Benzylpiperidin-4-yl)-3-hydroxy-1-(2-methyl-1,3-benzothiazol-6-yl)propan-1-one
• 化学式: C₂₃H₂₆N₂O₂S
• 分子量: 394.538
• InChiKey: JAXBMZGJJUGSAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(1-benzylpiperidin-4-yl)-3-hydroxy-1-(2-methylbenzothiazol-6-yl)propan-1-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 12.0h， 以67%的产率得到1-(2-methyl-6-benzothiazolyl)-3-(N-benzyl-4-piperidinyl)-2-propen-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-(2-甲基-1,3-苯并噻唑-6-基)乙酮 、 1-苄基-4-哌啶甲醛 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以90%的产率得到3-(1-benzylpiperidin-4-yl)-3-hydroxy-1-(2-methylbenzothiazol-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