1-(1-ethyl-2-methyl-5-benzimidazolyl)-3-(N-benzyl-4-piperidinyl)-2-propen-1-one | 163726-69-0

• 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-(1-ethyl-2-methyl-5-benzimidazolyl)-3-(N-benzyl-4-piperidinyl)-2-propen-1-one
• 英文别名: 1-(1-Ethyl-2-methyl-1H-benzimidazol-5-yl)-3-[(1-phenylmethyl)-4-piperidinyl]-2-propen-1-one；(E)-3-(1-benzylpiperidin-4-yl)-1-(1-ethyl-2-methylbenzimidazol-5-yl)prop-2-en-1-one
• CAS: 163726-69-0
• 化学式: C₂₅H₂₉N₃O
• 分子量: 387.525
• InChiKey: STZOMUXKQIDEMV-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-ethyl-2-methyl-5-benzimidazolyl)-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， 以72%的产率得到1-(1-ethyl-2-methyl-1H-benzimidazol-5-yl)-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)-1-(1-ethyl-2-methyl-1H-benzimidazol-5-yl)-3-hydroxypropan-1-one 在 ethyl(carboxysulfamoyl)triethylammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以89%的产率得到1-(1-ethyl-2-methyl-5-benzimidazolyl)-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：Pfizer Inc.

  公开号：US05574046A1

  公开（公告）日：1996-11-12

  Compounds of the formula ##STR1## wherein ring A, ring B, ring D, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.11, R.sup.12, R.sup.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.

  式##STR1##中的化合物，其中环A、环B、环D、R.sup.2、R.sup.3、R.sup.4、R.sup.5、R.sup.6、R.sup.11、R.sup.12、R.sup.13、E、G、X和P的定义如下。式I的化合物是胆碱酯酶抑制剂，对患有痴呆症和阿尔茨海默病的患者有助于增强记忆。
• 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
• US6124321A
  申请人：——

  公开号：US6124321A

  公开（公告）日：2000-09-26
• US6303633B1
  申请人：——

  公开号：US6303633B1

  公开（公告）日：2001-10-16