(E)-3-(4-ethylphenyl)-1-(4-morpholin-4-ylphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(4-ethylphenyl)-1-(4-morpholin-4-ylphenyl)prop-2-en-1-one
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: FXQLKLZWEUEWLA-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(4-吗啉基)苯乙酮 、 4-乙基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-3-(4-ethylphenyl)-1-(4-morpholin-4-ylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Morpholine-based chalcones as dual-acting monoamine oxidase-B and acetylcholinesterase inhibitors: synthesis and biochemical investigations

  摘要：

  Nine compounds (MO1-MO9) containing the morpholine moiety were assessed for their inhibitory activities against monoamine oxidases (MAOs) and acetylcholinesterase (AChE). Most of the compounds potently inhibited MAO-B; MO1 most potently inhibited with an IC₅₀ value of 0.030 µM, followed by MO7 (0.25 µM). MO5 most potently inhibited AChE (IC₅₀ = 6.1 µM), followed by MO9 (IC₅₀ = 12.01 µM) and MO7 most potently inhibited MAO-A (IC₅₀ = 7.1 µM). MO1 was a reversible mixed-type inhibitor of MAO-B (K_i = 0.018 µM); MO5 reversibly competitively inhibited AChE (K_i = 2.52 µM); and MO9 reversibly noncompetitively inhibited AChE (K_i = 7.04 µM). MO1, MO5 and MO9 crossed the blood-brain barrier, and were non-toxic to normal VERO cells. These results show that MO1 is a selective inhibitor of MAO-B and that MO5 is a dual-acting inhibitor of AChE and MAO-B, and that both should be considered candidates for the treatment of Alzheimer's disease.

  DOI：

  10.1080/14756366.2020.1842390

文献信息

• Morpholine-based chalcones as dual-acting monoamine oxidase-B and acetylcholinesterase inhibitors: synthesis and biochemical investigations
  作者：Rani Sasidharan、Bo Hyun Eom、Jeong Hyun Heo、Jong Eun Park、Mohamed A. Abdelgawad、Arafa Musa、Nicola Gambacorta、Orazio Nicolotti、Sreedharannair Leelabaiamma Manju、Bijo Mathew、Hoon Kim

  DOI：10.1080/14756366.2020.1842390

  日期：2021.1.1

  Nine compounds (MO1-MO9) containing the morpholine moiety were assessed for their inhibitory activities against monoamine oxidases (MAOs) and acetylcholinesterase (AChE). Most of the compounds potently inhibited MAO-B; MO1 most potently inhibited with an IC₅₀ value of 0.030 µM, followed by MO7 (0.25 µM). MO5 most potently inhibited AChE (IC₅₀ = 6.1 µM), followed by MO9 (IC₅₀ = 12.01 µM) and MO7 most potently inhibited MAO-A (IC₅₀ = 7.1 µM). MO1 was a reversible mixed-type inhibitor of MAO-B (K_i = 0.018 µM); MO5 reversibly competitively inhibited AChE (K_i = 2.52 µM); and MO9 reversibly noncompetitively inhibited AChE (K_i = 7.04 µM). MO1, MO5 and MO9 crossed the blood-brain barrier, and were non-toxic to normal VERO cells. These results show that MO1 is a selective inhibitor of MAO-B and that MO5 is a dual-acting inhibitor of AChE and MAO-B, and that both should be considered candidates for the treatment of Alzheimer's disease.