6-(6,8-dichloro-1,2,3,4-tetrahydroacridin-9-ylamino)hexanoic acid pentyl ester | 873445-29-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-(6,8-dichloro-1,2,3,4-tetrahydroacridin-9-ylamino)hexanoic acid pentyl ester
• CAS: 873445-29-5
• 化学式: C₂₄H₃₂Cl₂N₂O₂
• 分子量: 451.436
• InChiKey: LGKBMEKYNCYMEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-(6,8-dichloro-1,2,3,4-tetrahydroacridin-9-ylamino)hexanoic acid pentyl ester 在 sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 6-(6,8-Dichloro-1,2,3,4-tetrahydro-acridin-9-ylamino)-hexanoic acid [2-(1H-indol-3-yl)-ethyl]-amide
  参考文献：
  名称：

  Novel Tacrine−Melatonin Hybrids as Dual-Acting Drugs for Alzheimer Disease, with Improved Acetylcholinesterase Inhibitory and Antioxidant Properties

  摘要：

  Tacrine and melatonin are well-known drugs with activities as an acetylcholinesterase (AChE) inhibitor and free radical scavenger, respectively. In this work, we report new hybrids of both drugs that display higher in vitro properties than the sum of their parts. As selective inhibitors of human AChE, their IC50 values range from sub-nanomolar to picomolar. They exhibit a higher oxygen radical absorbance capacity than does melatonin and are predicted to be able to cross the blood-brain barrier to reach their targets in the central nervous system.

  DOI：

  10.1021/jm050746d
• 作为产物：
  描述：

  戊醇 、 6,8,9-trichloro-1,2,3,4-tetrahydroacridine 、 6-氨基己酸 以85%的产率得到6-(6,8-dichloro-1,2,3,4-tetrahydroacridin-9-ylamino)hexanoic acid pentyl ester
  参考文献：
  名称：

  Novel Tacrine−Melatonin Hybrids as Dual-Acting Drugs for Alzheimer Disease, with Improved Acetylcholinesterase Inhibitory and Antioxidant Properties

  摘要：

  Tacrine and melatonin are well-known drugs with activities as an acetylcholinesterase (AChE) inhibitor and free radical scavenger, respectively. In this work, we report new hybrids of both drugs that display higher in vitro properties than the sum of their parts. As selective inhibitors of human AChE, their IC50 values range from sub-nanomolar to picomolar. They exhibit a higher oxygen radical absorbance capacity than does melatonin and are predicted to be able to cross the blood-brain barrier to reach their targets in the central nervous system.

  DOI：

  10.1021/jm050746d