(E)-3-(2-(trifluoromethyl)phenyl)-N-(3-hydroxyphenyl)-2-propenamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(2-(trifluoromethyl)phenyl)-N-(3-hydroxyphenyl)-2-propenamide
• 英文别名: (E)-N-(3-hydroxyphenyl)-3-[2-(trifluoromethyl)phenyl]prop-2-enamide
• 化学式: C₁₆H₁₂F₃NO₂
• 分子量: 307.272
• InChiKey: NVXUFYXBTGRDND-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(三氟甲基)肉桂酸 、 3-氨基苯酚 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.12h， 以40%的产率得到(E)-3-(2-(trifluoromethyl)phenyl)-N-(3-hydroxyphenyl)-2-propenamide
  参考文献：
  名称：

  Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors

  摘要：

  We have synthesized three categories of alpha,beta-unsaturated carbonyl derivatives and evaluated their MAO-A and MAO-B inhibitory activities. Among them, compound 10b including alpha, beta-unsaturated ketone group showed the most potent and selective MAO-B inhibitory activity (IC50 human MAO-B 16 nM, >6000-fold selective vs MAO-A) and compound 10b exhibited good reversibility compared with selegiline, a well-known irreversible MAO-B inhibitor. However, both a, b-unsaturated amide and ester derivatives exhibited weaker MAO-B inhibition potencies. The docking studies provided insights into the possible binding modes and the key interaction sites of the synthesized MAO-B inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.08.012

文献信息

• Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors
  作者：Ji Won Choi、Bo Ko Jang、Nam-chul Cho、Jong-Hyun Park、Seul Ki Yeon、Eun Ji Ju、Yong Sup Lee、Gyoonhee Han、Ae Nim Pae、Dong Jin Kim、Ki Duk Park

  DOI：10.1016/j.bmc.2015.08.012

  日期：2015.10

  We have synthesized three categories of alpha,beta-unsaturated carbonyl derivatives and evaluated their MAO-A and MAO-B inhibitory activities. Among them, compound 10b including alpha, beta-unsaturated ketone group showed the most potent and selective MAO-B inhibitory activity (IC50 human MAO-B 16 nM, >6000-fold selective vs MAO-A) and compound 10b exhibited good reversibility compared with selegiline, a well-known irreversible MAO-B inhibitor. However, both a, b-unsaturated amide and ester derivatives exhibited weaker MAO-B inhibition potencies. The docking studies provided insights into the possible binding modes and the key interaction sites of the synthesized MAO-B inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.