2-[[3-(1,2,3,4-Tetrahydroacridin-9-ylamino)propylamino]methyl]phenol | 1400585-25-2

• 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: 2-[[3-(1,2,3,4-Tetrahydroacridin-9-ylamino)propylamino]methyl]phenol
• 英文别名: 2-[[3-(1,2,3,4-tetrahydroacridin-9-ylamino)propylamino]methyl]phenol
• CAS: 1400585-25-2
• 化学式: C₂₃H₂₇N₃O
• 分子量: 361.487
• InChiKey: PXIRZFSARGCTPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  9-氯-1,2,3,4-四氢吖啶 在 potassium iodide 作用下， 以 乙醇 、 戊醇 为溶剂， 反应 7.08h， 生成 2-[[3-(1,2,3,4-Tetrahydroacridin-9-ylamino)propylamino]methyl]phenol
  参考文献：
  名称：

  O-Hydroxyl- or o-amino benzylamine-tacrine hybrids: Multifunctional biometals chelators, antioxidants, and inhibitors of cholinesterase activity and amyloid-β aggregation

  摘要：

  In an effort to identify novel multifunctional drug candidates for the treatment of Alzheimer's disease (AD), a series of hybrid molecules were synthesised by reacting N-(aminoalkyl)tacrine with salicylic aldehyde or derivatives of 2-aminobenzaldehyde. These compounds were then evaluated as multifunctional anti-Alzheimer's disease agents. All of the hybrids are potential biometal chelators, and in addition, most of them were better antioxidants and inhibitors of cholinesterases and amyloid-beta (A beta) aggregation than the lead compound tacrine. Compound 7c has the potential to be a candidate for AD therapy: it is a much better inhibitor of acetylcholinesterase (AChE) than tacrine (IC50: 0.55 nM vs 109 nM), has good biometal chelation ability, is able to inhibit A beta aggregation and has moderate antioxidant activity (1.22 Trolox equivalents). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.045

文献信息

• O-Hydroxyl- or o-amino benzylamine-tacrine hybrids: Multifunctional biometals chelators, antioxidants, and inhibitors of cholinesterase activity and amyloid-β aggregation
  作者：Fei Mao、Ling Huang、Zonghua Luo、Anqiu Liu、Chuanjun Lu、Zhiyong Xie、Xingshu Li

  DOI：10.1016/j.bmc.2012.07.045

  日期：2012.10

  In an effort to identify novel multifunctional drug candidates for the treatment of Alzheimer's disease (AD), a series of hybrid molecules were synthesised by reacting N-(aminoalkyl)tacrine with salicylic aldehyde or derivatives of 2-aminobenzaldehyde. These compounds were then evaluated as multifunctional anti-Alzheimer's disease agents. All of the hybrids are potential biometal chelators, and in addition, most of them were better antioxidants and inhibitors of cholinesterases and amyloid-beta (A beta) aggregation than the lead compound tacrine. Compound 7c has the potential to be a candidate for AD therapy: it is a much better inhibitor of acetylcholinesterase (AChE) than tacrine (IC50: 0.55 nM vs 109 nM), has good biometal chelation ability, is able to inhibit A beta aggregation and has moderate antioxidant activity (1.22 Trolox equivalents). (C) 2012 Elsevier Ltd. All rights reserved.