(E)-1-(3-amino-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)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)-1-(3-amino-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: MMRXOIFFSOFCAN-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-amino-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 、 2-溴-5-甲氧基苯甲醛 以 甲醇 为溶剂， 以70.2%的产率得到(E)-1-{3-[(E)-(2-bromo-5-methoxybenzylidene)amino]-4-methoxyphenyl}-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of paralleled Aza resveratrol–chalcone compounds as potential anti-inflammatory agents for the treatment of acute lung injury

  摘要：

  Acute lung injury (ALI) is a major cause of acute respiratory failure in critically-ill patients. It has been reported that both resveratrol and chalcone derivatives could ameliorate lung injury induced by inflammation. A series of paralleled Aza resveratrol-chalcone compounds (5a-5m, 6a-6i) were designed, synthesized and screened for anti-inflammatory activity. A majority showed potent inhibition on the IL-6 and TNF-alpha expression-stimulated by LPS in macrophages, of which compound 6b is the most potent analog by inhibition of LPS-induced IL-6 release in a dose-dependent manner. Moreover, 6b exhibited protection against LPS-induced acute lung injury in vivo. These results offer further insight into the use of Aza resveratrol-chalcone compounds for the treatment of inflammatory diseases, and the use of compound 6b as a lead compound for the development of anti-ALI agents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.05.030
• 作为产物：
  描述：

  4-甲氧基-3-硝基苯乙酮 在 sodium hydroxide 、 tin(ll) chloride 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 (E)-1-(3-amino-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  硝基和氨基查耳酮的合成及其细胞毒性

  摘要：

  合成并表征了22个硝基和氨基查耳酮。通过用鼠黑素瘤B16细胞进行3天连续暴露MTT测定来确定它们的细胞毒性特性。氨基查耳酮通常比其硝基前体更具细胞毒性。IC50值为0.24μM的氨基查耳酮18是最有效的化合物。结果表明，环A中甲氧基的数量和位置增强了查耳酮的细胞毒性。B环上氨基的位置也影响细胞毒性。

  DOI：

  10.1007/s00044-004-0122-7