3-phenyl-1-(2,4,6-trimethoxy-phenyl)-but-2c-en-1-one | 147729-73-5

• 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: 3-phenyl-1-(2,4,6-trimethoxy-phenyl)-but-2c-en-1-one
• 英文别名: 3-Phenyl-1-(2,4,6-trimethoxy-phenyl)-but-2c-en-1-on；(E)-3-phenyl-1-(2,4,6-trimethoxyphenyl)but-2-en-1-one
• CAS: 147729-73-5
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: SLVPJSYAMHRGLM-JLHYYAGUSA-N

物化性质

• 沸点：
  478.0±45.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-(2,4,6-trimethoxy-phenyl)-but-2c-en-1-one 在 aluminum tri-bromide 、 苯 作用下， 生成 1-(2-hydroxy-4,6-dimethoxy-phenyl)-3-phenyl-but-2c-en-1-one
  参考文献：
  名称：

  Gripenberg et al., Acta Chemica Scandinavica (1947), 1956, vol. 10, p. 393,396

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3,5-三甲氧基苯 、 3-phenylbut-2-enoyl chloride 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以67%的产率得到3-phenyl-1-(2,4,6-trimethoxy-phenyl)-but-2c-en-1-one
  参考文献：
  名称：

  2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis

  摘要：

  A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1beta from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-muM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings beta to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.

  DOI：

  10.1021/jm00062a016

文献信息

• 2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis
  作者：Douglas G. Batt、Robin Goodman、David G. Jones、Janet S. Kerr、Lisa R. Mantegna、Candice McAllister、Robert C. Newton、Sherrill Nurnberg、Patricia K. Welch、Maryanne B. Covington

  DOI：10.1021/jm00062a016

  日期：1993.5

  A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1beta from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-muM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings beta to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.
• Gripenberg et al., Acta Chemica Scandinavica (1947), 1956, vol. 10, p. 393,396
  作者：Gripenberg et al.

  DOI：——

  日期：——