(1E,4E)-1,5-bis(2-fluoro-6-(trifluoromethyl)phenyl)penta-1,4-dien-3-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E,4E)-1,5-bis(2-fluoro-6-(trifluoromethyl)phenyl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1,5-bis[2-fluoro-6-(trifluoromethyl)phenyl]penta-1,4-dien-3-one
• 化学式: C₁₉H₁₀F₈O
• 分子量: 406.275
• InChiKey: ZDPFHZWDONSKTC-FIFLTTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-氟-6-(三氟甲基)苯甲醛 、 丙酮 在 甲醇 、 sodium methylate 作用下， 以65.2%的产率得到(1E,4E)-1,5-bis(2-fluoro-6-(trifluoromethyl)phenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis and anti-inflammatory evaluation of novel mono-carbonyl analogues of curcumin in LPS-stimulated RAW 264.7 macrophages

  摘要：

  Curcumin is a multifunctional natural product with regulatory effects on inflammation. However, a major limitation for the application of curcumin is its poor bioavailability. We previously demonstrated that the mono-carbonyl analogues of curcumin possessed improved pharmacokinetic profiles. In this study, 33 novel mono-carbonyl analogues of curcumin were synthesized and their inhibition against TNF-alpha and IL-6 release was evaluated in LPS-stimulated RAW 264.7 macrophages. Based on the screening data, quantitative structure activity relationship was conducted, indicating that electron-withdrawing groups in benzene ring are favourable to anti-inflammatory activities of B-class compounds. Furthermore, compounds AN1 and 1382 demonstrated anti-inflammatory abilities in a dose-dependent manner. These raise the possibility that these compounds might serve as potential agents for the treatment of inflammatory diseases. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.037

文献信息

• Synthesis and anti-inflammatory evaluation of novel mono-carbonyl analogues of curcumin in LPS-stimulated RAW 264.7 macrophages
  作者：Chengguang Zhao、Yuepiao Cai、Xuzhi He、Jianling Li、Li Zhang、Jianzhang Wu、Yunjie Zhao、Shulin Yang、Xiaokun Li、Wulan Li、Guang Liang

  DOI：10.1016/j.ejmech.2010.09.037

  日期：2010.12

  Curcumin is a multifunctional natural product with regulatory effects on inflammation. However, a major limitation for the application of curcumin is its poor bioavailability. We previously demonstrated that the mono-carbonyl analogues of curcumin possessed improved pharmacokinetic profiles. In this study, 33 novel mono-carbonyl analogues of curcumin were synthesized and their inhibition against TNF-alpha and IL-6 release was evaluated in LPS-stimulated RAW 264.7 macrophages. Based on the screening data, quantitative structure activity relationship was conducted, indicating that electron-withdrawing groups in benzene ring are favourable to anti-inflammatory activities of B-class compounds. Furthermore, compounds AN1 and 1382 demonstrated anti-inflammatory abilities in a dose-dependent manner. These raise the possibility that these compounds might serve as potential agents for the treatment of inflammatory diseases. (C) 2010 Elsevier Masson SAS. All rights reserved.