N-(5-hydrazino-5-oxopentyl)-3-(3,4,5-trimethoxyphenyl)propanamide | 918494-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(5-hydrazino-5-oxopentyl)-3-(3,4,5-trimethoxyphenyl)propanamide
• 英文别名: N-(5-hydrazinyl-5-oxopentyl)-3-(3,4,5-trimethoxyphenyl)propanamide
• CAS: 918494-62-9
• 化学式: C₁₇H₂₇N₃O₅
• 分子量: 353.418
• InChiKey: KAWONFRHQBFIQT-UHFFFAOYSA-N

物化性质

• 熔点：
  123-126 °C(Solv: ethanol (64-17-5))
• 沸点：
  628.9±55.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(5-hydrazino-5-oxopentyl)-3-(3,4,5-trimethoxyphenyl)propanamide 、 9-氯-1,2,3,4-四氢吖啶 以 乙醇 为溶剂， 反应 24.0h， 以53%的产率得到3-(3,4,5-trimethoxyphenyl)-N-(5-oxo-5-(2-(1,2,3,4-tetrahydroacridin-9-yl)hydrazino)-pentyl)propanamide
  参考文献：
  名称：

  Novel Heterobivalent Tacrine Derivatives as Cholinesterase Inhibitors with Notable Selectivity Toward Butyrylcholinesterase

  摘要：

  Two series of novel heterobivalent tacrine derivatives were synthesized. A trimethoxy substituted benzene was linked to the tacrine moiety by a hydrazide-based linker. The compounds were evaluated as cholinesterase inhibitors, and trimethoxybenzoic acid derivatives with 11- or 12-atom spacers were the most potent inhibitors of human acetylcholinesterase. The inhibitors showed a surprising selectivity toward human butyrylcholinesterase, where several trimethoxyphenylpropionic acid derivatives had IC50 values less than 250 mu M.

  DOI：

  10.1021/jm060742o
• 作为产物：
  描述：

  5-氨基颉草酸 在 氯化亚砜 、 一水合肼 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 N-(5-hydrazino-5-oxopentyl)-3-(3,4,5-trimethoxyphenyl)propanamide
  参考文献：
  名称：

  Novel Heterobivalent Tacrine Derivatives as Cholinesterase Inhibitors with Notable Selectivity Toward Butyrylcholinesterase

  摘要：

  Two series of novel heterobivalent tacrine derivatives were synthesized. A trimethoxy substituted benzene was linked to the tacrine moiety by a hydrazide-based linker. The compounds were evaluated as cholinesterase inhibitors, and trimethoxybenzoic acid derivatives with 11- or 12-atom spacers were the most potent inhibitors of human acetylcholinesterase. The inhibitors showed a surprising selectivity toward human butyrylcholinesterase, where several trimethoxyphenylpropionic acid derivatives had IC50 values less than 250 mu M.

  DOI：

  10.1021/jm060742o

文献信息

• Novel Heterobivalent Tacrine Derivatives as Cholinesterase Inhibitors with Notable Selectivity Toward Butyrylcholinesterase
  作者：Paul W. Elsinghorst、Camino M. González Tanarro、Michael Gütschow

  DOI：10.1021/jm060742o

  日期：2006.12.1

  Two series of novel heterobivalent tacrine derivatives were synthesized. A trimethoxy substituted benzene was linked to the tacrine moiety by a hydrazide-based linker. The compounds were evaluated as cholinesterase inhibitors, and trimethoxybenzoic acid derivatives with 11- or 12-atom spacers were the most potent inhibitors of human acetylcholinesterase. The inhibitors showed a surprising selectivity toward human butyrylcholinesterase, where several trimethoxyphenylpropionic acid derivatives had IC50 values less than 250 mu M.