1-(2-methyl-6-benzothiazolyl)-3-(N-benzyl-4-piperidinyl)-2-propen-1-one | 163726-70-3

• 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-(2-methyl-6-benzothiazolyl)-3-(N-benzyl-4-piperidinyl)-2-propen-1-one
• 英文别名: 1-(2-Methyl-6-benzothiazolyl)-3-[1-(phenylmethyl)-4-piperidinyl]-2-propen-1-one；(E)-3-(1-benzylpiperidin-4-yl)-1-(2-methyl-1,3-benzothiazol-6-yl)prop-2-en-1-one
• CAS: 163726-70-3
• 化学式: C₂₃H₂₄N₂OS
• 分子量: 376.522
• InChiKey: HCRDJIXLTOLBFE-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-methyl-6-benzothiazolyl)-3-(N-benzyl-4-piperidinyl)-2-propen-1-one 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 1-(2-methyl-6-benzothiazolyl)-3-[1-(phenylmethyl)-4-piperidinyl]-1-propanone
  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：

  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

文献信息

• Heteroaryl amines as novel acetylcholinesterase inhibitors
  申请人：——

  公开号：US20020049210A1

  公开（公告）日：2002-04-25

  Compounds of the formula 1 wherein ring A, ring B, ring D, R 2 , R 3 , R 4 , R 5 , R 6 ,R 11 , R 12 , R 13 , E, G, X and P are as defined below. The compounds of formula I are cholinesterase inhibitors and are useful in enhancing memory in patients suffering from dementia and Alzheimer's disease.

  化合物的公式为1，其中环A、环B、环D、R2、R3、R4、R5、R6、R11、R12、R13、E、G、X和P的定义如下。式I的化合物是胆碱酯酶抑制剂，对于患有痴呆症和阿尔茨海默病的患者增强记忆力具有有用的作用。
• A pharmaceutical composition for the prevention and treatment of diseases of cognitive dysfunction in a mammal
  申请人：Pfizer Products Inc.

  公开号：EP0976404A2

  公开（公告）日：2000-02-02

  Pharmaceutical compositions for the treatment of diseases involving cognitive dysfunction in a mammal comprising an estrogen agonist or antagonist or a pharmaceutically acceptable salt thereof; an acetyl cholinesterase inhibitor or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable carrier. The estrogen agonists or antagonists and acetylcholinesterase inhibitors are present in amounts that render the composition effective in the treatment of diseases of cognitive dysfunction including Alzheimer's Disease and Dementia. The method of using these composition is also disclosed. The compositions may help memory inhancement.

  用于治疗哺乳动物认知功能障碍疾病的药物组合物，包含雌激素激动剂或拮抗剂或其药学上可接受的盐；乙酰胆碱酯酶抑制剂或其药学上可接受的盐；以及药学上可接受的载体。雌激素激动剂或拮抗剂和乙酰胆碱酯酶抑制剂的含量可使组合物有效治疗认知功能障碍疾病，包括阿尔茨海默病和痴呆症。还公开了使用这些组合物的方法。这些组合物有助于增强记忆力。
• HETEROARYL AMINES AS NOVEL ACETYL CHOLINESTERASE INHIBITORS
  申请人：Eisai Co., Ltd.

  公开号：EP0606248B1

  公开（公告）日：2003-03-26
• US5574046A
  申请人：——

  公开号：US5574046A

  公开（公告）日：1996-11-12
• US5965574A
  申请人：——

  公开号：US5965574A

  公开（公告）日：1999-10-12