(E)-4-[3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxopropene-1-yl]phenylacetamide | 919092-47-0

• 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)-4-[3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxopropene-1-yl]phenylacetamide
• 英文别名: N-[4-[(E)-3-[2-(cyclohexylmethoxy)-6-hydroxyphenyl]-3-oxoprop-1-enyl]phenyl]acetamide
• CAS: 919092-47-0
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: AUQURHBOSXCCLV-NTCAYCPXSA-N

物化性质

• 熔点：
  203.0-204.0 °C
• 沸点：
  658.6±55.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-[3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxopropene-1-yl]phenylacetamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以75.2%的产率得到(E)-3-(4-aminophenyl)-1-[2-(cyclohexylmethoxy)-6-hydroxyphenyl]prop-2-en-1-one
  参考文献：
  名称：

  Structural requirement of chalcones for the inhibitory activity of interleukin-5

  摘要：

  Novel chalcones were found as potent inhibitors of interleukin (IL)-5. 1-(2-Benzyloxy-6-hydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one (2b, 78.8% inhibition at 50 mu M, IC50 = 25.3 mu M) was initially identified as a potent inhibitor of IL-5. This shows the compatible activity with budesonide or sophoricoside. To identify structural requirements, 26 chalcones were prepared and their inhibitory activities were tested against IL-5. Among them, compound 4-[(E)-3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxoprop-1-enyl]benzenesulfonamide (2w, 99.5% inhibition at 50 mu M, IC50 = 1-8 mu M) shows the most potent activity. The important structural requirements of these chalcone analogs exhibiting the inhibitory activity against IL-5 were recognized as the following. (1) The hydrophobic group such as benzyloxy or cyclohexylmethoxy at 6-position of A ring is necessary. (2) The existence of phenolic hydroxyl at 6-position of A ring is critical. (3) Propenone unit as alpha,beta-unsaturated ketone is essential. (4) Electron withdrawing groups with hydrogen acceptor property at 4-position of B ring enhance the activity and quantitative structure-activity relationship of 2 regarding these substituents was determined. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.007
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 3.75h， 生成 (E)-4-[3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxopropene-1-yl]phenylacetamide
  参考文献：
  名称：

  Structural requirement of chalcones for the inhibitory activity of interleukin-5

  摘要：

  Novel chalcones were found as potent inhibitors of interleukin (IL)-5. 1-(2-Benzyloxy-6-hydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one (2b, 78.8% inhibition at 50 mu M, IC50 = 25.3 mu M) was initially identified as a potent inhibitor of IL-5. This shows the compatible activity with budesonide or sophoricoside. To identify structural requirements, 26 chalcones were prepared and their inhibitory activities were tested against IL-5. Among them, compound 4-[(E)-3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxoprop-1-enyl]benzenesulfonamide (2w, 99.5% inhibition at 50 mu M, IC50 = 1-8 mu M) shows the most potent activity. The important structural requirements of these chalcone analogs exhibiting the inhibitory activity against IL-5 were recognized as the following. (1) The hydrophobic group such as benzyloxy or cyclohexylmethoxy at 6-position of A ring is necessary. (2) The existence of phenolic hydroxyl at 6-position of A ring is critical. (3) Propenone unit as alpha,beta-unsaturated ketone is essential. (4) Electron withdrawing groups with hydrogen acceptor property at 4-position of B ring enhance the activity and quantitative structure-activity relationship of 2 regarding these substituents was determined. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.007