3-((8-(1,2,3,4-tetrahydroacridin-9-ylamino)octylamino)methyl)phenol | 1310089-91-8

• 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: 3-((8-(1,2,3,4-tetrahydroacridin-9-ylamino)octylamino)methyl)phenol
• 英文别名: 3-[[8-(1,2,3,4-tetrahydroacridin-9-ylamino)octylamino]methyl]phenol
• CAS: 1310089-91-8
• 化学式: C₂₈H₃₇N₃O
• 分子量: 431.621
• InChiKey: MFONRPQRCLNWME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  spiro[2H-3,1-benzoxazine-2,1'-cyclohexan]-4(1H)-one 在 sodium tetrahydroborate 、 potassium iodide 、 三氯氧磷 作用下， 以 甲醇 、 戊醇 为溶剂， 反应 8.0h， 生成 3-((8-(1,2,3,4-tetrahydroacridin-9-ylamino)octylamino)methyl)phenol
  参考文献：
  名称：

  Synthesis and evaluation of heterobivalent tacrine derivatives as potential multi-functional anti-Alzheimer agents

  摘要：

  A new series of heterobivalent tacrine derivatives were designed, synthesized and evaluated as potential multi-functional anti-Alzheimer agents for their inhibitory activity on cholinesterases, antioxidant activity and self-induced beta-amyloid (A beta) aggregation. All these synthesized compounds had potent inhibition activity on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) at nanomolar range. A Lineweaver-Burk plot and molecular modeling study showed that these compounds targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. The compounds containing hydroxyl group showed potent peroxyl radical absorbance activity. In addition, compound 5j exhibited higher self-induced A beta aggregation inhibitory activity than curcumin, which could become a multifunctional agent for further development for the treatment of AD. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.058

文献信息

• Synthesis and evaluation of heterobivalent tacrine derivatives as potential multi-functional anti-Alzheimer agents
  作者：Wen Luo、Yan-Ping Li、Yan He、Shi-Liang Huang、Ding Li、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.ejmech.2011.03.058

  日期：2011.6

  A new series of heterobivalent tacrine derivatives were designed, synthesized and evaluated as potential multi-functional anti-Alzheimer agents for their inhibitory activity on cholinesterases, antioxidant activity and self-induced beta-amyloid (A beta) aggregation. All these synthesized compounds had potent inhibition activity on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) at nanomolar range. A Lineweaver-Burk plot and molecular modeling study showed that these compounds targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. The compounds containing hydroxyl group showed potent peroxyl radical absorbance activity. In addition, compound 5j exhibited higher self-induced A beta aggregation inhibitory activity than curcumin, which could become a multifunctional agent for further development for the treatment of AD. (C) 2011 Elsevier Masson SAS. All rights reserved.