2-acetyl-5-(3-phenylpropoxy)phenol | 63359-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetyl-5-(3-phenylpropoxy)phenol
• 英文别名: 1-[2-Hydroxy-4-(3-phenylpropoxy)phenyl]ethanone
• CAS: 63359-86-4
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: JLKHSNNXQDGNQA-UHFFFAOYSA-N

物化性质

• 熔点：
  75–77°C
• 沸点：
  455.1±35.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4-二羟基苯乙酮 、 1-溴-3-苯基丙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以61%的产率得到2-acetyl-5-(3-phenylpropoxy)phenol
  参考文献：
  名称：

  2-acetylphenol analogs as potent reversible monoamine oxidase inhibitors

  摘要：

  Based on a previous report that substituted 2-acetylphenols may be promising leads for the design of novel monoamine oxidase (MAO) inhibitors, a series of C5-substituted 2-acetylphenol analogs (15) and related compounds (two) were synthesized and evaluated as inhibitors of human MAO-A and MAO-B. Generally, the study compounds exhibited inhibitory activities against both MAO-A and MAO-B, with selectivity for the B isoform. Among the compounds evaluated, seven compounds exhibited IC50 values <0.01 mu M for MAO-B inhibition, with the most selective compound being 17,000-fold selective for MAO-B over the MAO-A isoform. Analyses of the structure-activity relationships for MAO inhibition show that substitution on the C5 position of the 2-acetylphenol moiety is a requirement for MAO-B inhibition, and the benzyloxy substituent is particularly favorable in this regard. This study concludes that C5-substituted 2-acetylphenol analogs are potent and selective MAO-B inhibitors, appropriate for the design of therapies for neurodegenerative disorders such as Parkinson's disease.

  DOI：

  10.2147/dddt.s86225

文献信息

• Aryloxyalkyloxy- and aralkyloxy-4-hydroxy-3-nitrocoumarins which inhibit histamine release in the rat and also antagonize the effects of a slow reacting substance of anaphylaxis
  作者：Derek R. Buckle、D. James Outred、Janet W. Ross、Harry Smith、Raymond J. Smith、Barbara A. Spicer、Brian C. Gasson

  DOI：10.1021/jm00188a007

  日期：1979.2

  The syntheses and structure--activity relationships of a number of 4-hydroxy-3-nitrocoumarins, which are both antagonists of a slow reacting substance of anaphylaxis and potent inhibitors of antigen-induced histamine release in the rat, are described. Most active among these are 7-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy(-2-hydroxypropoxy] derivatives having hydrogen or lower alkyl substituents at the C-8 position of the coumarin ring, 168, 171, 173, and 174.