(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

文献信息

• SYNTHESIS AND CYTOTOXIC PROPERTIES OF NITRO- AND AMINOCHALCONES
  作者：Hari N. Pati、Herman L. Holt、Regan LeBlanc、John Dickson、Michelle Stewart、Toni Brown、Moses Lee

  DOI：10.1007/s00044-004-0122-7

  日期：2005.1

  Twenty-two nitro- and aminochalcones were synthesized and characterized. Their cytotoxic properties were determined by a 3-day continuous exposure MTT assay with murine melanoma B16 cells. The aminochalcones were generally more cytotoxic than their nitro precursors. Aminochalcone 18, which has an IC50 value of 0.24 μM, was the most potent compound. The results demonstrated that the number and position

  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。
• Design, synthesis and biological evaluation of paralleled Aza resveratrol–chalcone compounds as potential anti-inflammatory agents for the treatment of acute lung injury
  作者：Wenbo Chen、Xiangting Ge、Fengli Xu、Yali Zhang、Zhiguo Liu、Jialing Pan、Jiao Song、Yuanrong Dai、Jianmin Zhou、Jianpeng Feng、Guang Liang

  DOI：10.1016/j.bmcl.2015.05.030

  日期：2015.8

  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.