7-{[7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptylamino]methyl}-quinolin-8-ol | 1234548-48-1

• 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: 7-{[7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptylamino]methyl}-quinolin-8-ol
• 英文别名: 7-{[7-(1,2,3,4-Tetrahydroacridin-9-ylamino)heptylamino]methyl}-quinolin-8-ol Dihydrochloride；7-[[7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptylamino]methyl]quinolin-8-ol
• CAS: 1234548-48-1
• 化学式: C₃₀H₃₆N₄O
• 分子量: 468.642
• InChiKey: UNCVWUOMIWFTQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  70.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-{[7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptylamino]methyl}-quinolin-8-ol 在 盐酸 作用下， 以 甲苯 为溶剂， 生成 7-{[7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptylamino]methyl}-quinolin-8-ol dihydrochloride
  参考文献：
  名称：

  Novel Tacrine−8-Hydroxyquinoline Hybrids as Multifunctional Agents for the Treatment of Alzheimer’s Disease, with Neuroprotective, Cholinergic, Antioxidant, and Copper-Complexing Properties

  摘要：

  Tacrine and PBT2 (an 8-hydroxyquinoline derivative) are well-known drugs that inhibit cholinesterases and decrease beta-amyloid (A beta) levels by complexation of redox-active metals, respectively. In this work, novel tacrine-8-hydroxyquinoline hybrids have been designed, synthesized, and evaluated as potential multifunctional drugs for the treatment of Alzheimer's disease. At nano- and subnanomolar concentrations they inhibit human acetyl- and butyrylcholinesterase (AChE and BuChE), being more potent than tacrine. They also displace propidium iodide from the peripheral anionic site of AChE and thus could be able to inhibit A beta aggregation promoted by AChE. They show better antioxidant properties than Trolox, the aromatic portion of vitamin E responsible for radical capture, and display neuroprotective properties against mitochondrial free radicals. In addition, they selectively complex Cu(II), show low cell toxicity, and could be able to penetrate the CNS, according to an in vitro blood brain barrier model.

  DOI：

  10.1021/jm100329q
• 作为产物：
  描述：

  8-羟基喹啉 、 聚合甲醛 、 N-(7-aminoheptyl)-1,2,3,4-tetrahydroacridin-9-amine 以 乙醇 为溶剂， 反应 6.0h， 以38%的产率得到7-{[7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptylamino]methyl}-quinolin-8-ol
  参考文献：
  名称：

  Novel Tacrine−8-Hydroxyquinoline Hybrids as Multifunctional Agents for the Treatment of Alzheimer’s Disease, with Neuroprotective, Cholinergic, Antioxidant, and Copper-Complexing Properties

  摘要：

  Tacrine and PBT2 (an 8-hydroxyquinoline derivative) are well-known drugs that inhibit cholinesterases and decrease beta-amyloid (A beta) levels by complexation of redox-active metals, respectively. In this work, novel tacrine-8-hydroxyquinoline hybrids have been designed, synthesized, and evaluated as potential multifunctional drugs for the treatment of Alzheimer's disease. At nano- and subnanomolar concentrations they inhibit human acetyl- and butyrylcholinesterase (AChE and BuChE), being more potent than tacrine. They also displace propidium iodide from the peripheral anionic site of AChE and thus could be able to inhibit A beta aggregation promoted by AChE. They show better antioxidant properties than Trolox, the aromatic portion of vitamin E responsible for radical capture, and display neuroprotective properties against mitochondrial free radicals. In addition, they selectively complex Cu(II), show low cell toxicity, and could be able to penetrate the CNS, according to an in vitro blood brain barrier model.

  DOI：

  10.1021/jm100329q

文献信息

• Novel Tacrine−8-Hydroxyquinoline Hybrids as Multifunctional Agents for the Treatment of Alzheimer’s Disease, with Neuroprotective, Cholinergic, Antioxidant, and Copper-Complexing Properties
  作者：María Isabel Fernández-Bachiller、Concepción Pérez、Gema C. González-Muñoz、Santiago Conde、Manuela G. López、Mercedes Villarroya、Antonio G. García、María Isabel Rodríguez-Franco

  DOI：10.1021/jm100329q

  日期：2010.7.8

  Tacrine and PBT2 (an 8-hydroxyquinoline derivative) are well-known drugs that inhibit cholinesterases and decrease beta-amyloid (A beta) levels by complexation of redox-active metals, respectively. In this work, novel tacrine-8-hydroxyquinoline hybrids have been designed, synthesized, and evaluated as potential multifunctional drugs for the treatment of Alzheimer's disease. At nano- and subnanomolar concentrations they inhibit human acetyl- and butyrylcholinesterase (AChE and BuChE), being more potent than tacrine. They also displace propidium iodide from the peripheral anionic site of AChE and thus could be able to inhibit A beta aggregation promoted by AChE. They show better antioxidant properties than Trolox, the aromatic portion of vitamin E responsible for radical capture, and display neuroprotective properties against mitochondrial free radicals. In addition, they selectively complex Cu(II), show low cell toxicity, and could be able to penetrate the CNS, according to an in vitro blood brain barrier model.