(E)-3-(3,4-dihydroxyphenyl)-N-[3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl]prop-2-enamide | 1408005-54-8

• 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: (E)-3-(3,4-dihydroxyphenyl)-N-[3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl]prop-2-enamide
• CAS: 1408005-54-8
• 化学式: C₂₅H₂₇N₃O₃
• 分子量: 417.508
• InChiKey: AEMIQXVCZRZSRZ-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  94.5
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  spiro[2H-3,1-benzoxazine-2,1'-cyclohexan]-4(1H)-one 在 4-二甲氨基吡啶 、 戊醇 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (E)-3-(3,4-dihydroxyphenyl)-N-[3-(1,2,3,4-tetrahydroacridin-9-ylamino)propyl]prop-2-enamide
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of novel tacrine–caffeic acid hybrids as multi-targeted compounds against Alzheimer’s disease

  摘要：

  A novel series of tacrine-caffeic acid hybrids (5a-f) were designed and synthesized by combining caffeic acid (CA) with tacrine. The antioxidant study revealed that all the hybrids have much more antioxidant capacities compared to CA. Among these compounds, 5e showed the highest selectivity in inhibiting acetylcholinesterase (AChE) over butyrylcholinesterase (BuChE). Enzyme kinetic study had suggested that 5e binds to both catalytic (CAS) and peripheral anionic sites (PAS) of AChE. Moreover, compound 5e also inhibited self- or AChE-induced beta-amyloid(1-40) aggregation, as well as had potent neuroprotective effects against H2O2- and glutamate- induced cell death with low toxicity in HT22 cells. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.036

文献信息

• Design, synthesis and pharmacological evaluation of novel tacrine–caffeic acid hybrids as multi-targeted compounds against Alzheimer’s disease
  作者：Xiaojuan Chao、Xixin He、Yilin Yang、Xie Zhou、Minghua Jin、Shu Liu、Zhiyi Cheng、Peiqing Liu、Yuting Wang、Jianchen Yu、Yi Tan、Yingjuan Huang、Jian Qin、Simona Rapposelli、Rongbiao Pi

  DOI：10.1016/j.bmcl.2012.08.036

  日期：2012.10

  A novel series of tacrine-caffeic acid hybrids (5a-f) were designed and synthesized by combining caffeic acid (CA) with tacrine. The antioxidant study revealed that all the hybrids have much more antioxidant capacities compared to CA. Among these compounds, 5e showed the highest selectivity in inhibiting acetylcholinesterase (AChE) over butyrylcholinesterase (BuChE). Enzyme kinetic study had suggested that 5e binds to both catalytic (CAS) and peripheral anionic sites (PAS) of AChE. Moreover, compound 5e also inhibited self- or AChE-induced beta-amyloid(1-40) aggregation, as well as had potent neuroprotective effects against H2O2- and glutamate- induced cell death with low toxicity in HT22 cells. (c) 2012 Elsevier Ltd. All rights reserved.