ethyl 2-methoxy-4-((1E)-3-oxo-3-{[2-(1,2,3,4-tetrahydroacridin-9-ylamino)ethyl]amino}prop-1-enyl)phenyl carbonate | 1036298-12-0

• 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: ethyl 2-methoxy-4-((1E)-3-oxo-3-{[2-(1,2,3,4-tetrahydroacridin-9-ylamino)ethyl]amino}prop-1-enyl)phenyl carbonate
• CAS: 1036298-12-0
• 化学式: C₂₈H₃₁N₃O₅
• 分子量: 489.571
• InChiKey: DKEGNSGHICRWQH-FYWRMAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  98.78
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-methoxy-4-((1E)-3-oxo-3-{[2-(1,2,3,4-tetrahydroacridin-9-ylamino)ethyl]amino}prop-1-enyl)phenyl carbonate 在 C.I.酸性橙108 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以89%的产率得到(E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(1,2,3,4-tetrahydroacridin-9-ylamino)ethyl]prop-2-enamide
  参考文献：
  名称：

  Design and synthesis of tacrine–ferulic acid hybrids as multi-potent anti-Alzheimer drug candidates

  摘要：

  Five tacrine-ferulic acid hybrids (6a-e) were designed and synthesized as multi-potent anti-Alzheimer drug candidates. All target compounds have better acetylcholinesterase inhibitory activity and comparable butyrylcholinesterase inhibitory activity in relation to tacrine. Interestingly, 6d showed a reversible and non-competitive inhibitory action for acetylcholinesterase indicating interaction with the peripheral anionic site, whereas a reversible but competitive inhibitory action for butyrylcholinesterase. The antioxidant study revealed that four target compounds have, compared to Trolox, high ability to absorb reactive oxygen species. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.073
• 作为产物：
  描述：

  (2E)-3-{4-[(ethoxycarbonyl)oxy]-3-methoxyphenyl}acrylic acid 、 9-(2-aminoethylamino)-1,2,3,4-tetrahydroacridine 在 N,N'-羰基二咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以42%的产率得到ethyl 2-methoxy-4-((1E)-3-oxo-3-{[2-(1,2,3,4-tetrahydroacridin-9-ylamino)ethyl]amino}prop-1-enyl)phenyl carbonate
  参考文献：
  名称：

  Design and synthesis of tacrine–ferulic acid hybrids as multi-potent anti-Alzheimer drug candidates

  摘要：

  Five tacrine-ferulic acid hybrids (6a-e) were designed and synthesized as multi-potent anti-Alzheimer drug candidates. All target compounds have better acetylcholinesterase inhibitory activity and comparable butyrylcholinesterase inhibitory activity in relation to tacrine. Interestingly, 6d showed a reversible and non-competitive inhibitory action for acetylcholinesterase indicating interaction with the peripheral anionic site, whereas a reversible but competitive inhibitory action for butyrylcholinesterase. The antioxidant study revealed that four target compounds have, compared to Trolox, high ability to absorb reactive oxygen species. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.073