(1E,4Z,6E)-5-hydroxy-1,7-bis(5-methylfuran-2-yl)hepta-1,4,6-trien-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (1E,4Z,6E)-5-hydroxy-1,7-bis(5-methylfuran-2-yl)hepta-1,4,6-trien-3-one
• 英文别名: 5-hydroxy-1,7-bis(5-methylfuran-2-yl)hepta-1,4,6-trien-3-one
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: LZBKLMJFWLHABZ-FBYAKURVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1E,6E)-1,7-bis(5-methylfuran-2-yl)hepta-1,6-diene-3,5-dione 在 盐酸 作用下， 以 水 为溶剂， 生成 (1E,4Z,6E)-5-hydroxy-1,7-bis(5-methylfuran-2-yl)hepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Synthesis and Identification of New 4-Arylidene Curcumin Analogues as Potential Anticancer Agents Targeting Nuclear Factor-κB Signaling Pathway

  摘要：

  A series of curcumin analogues including new 4-arylidene curcumin analogues (4-arylidene-1,7-bisarylhepta-1,6-diene-3,5-diones) were synthesized. Cell growth inhibition assays revealed that most 4-arylidene curcumin analogues can effectively decrease the growth of a panel of lung cancer cells at submicromolar and low micromolar concentrations. High content analysis technology coupled with biochemical studies showed that this new class of 4-arylidene curcumin analogues exhibits significantly improved NF-kappa B inhibition activity over the parent compound curcumin, at least in part by inhibiting I kappa B phosphorylation and degradation via IKK blockage; selected 4-arylidene curcumin analogues also reduced the tumorigenic potential of cancer cells in a clonogenic assay.

  DOI：

  10.1021/jm1004545

文献信息

• Synthesis and evaluation of curcumin analogues as potential thioredoxin reductase inhibitors
  作者：Xu Qiu、Zhong Liu、Wei-Yan Shao、Xing Liu、Da-Ping Jing、Yan-Jun Yu、Lin-Kun An、Shi-Liang Huang、Xian-Zhang Bu、Zhi-Shu Huang、Lian-Quan Gu

  DOI：10.1016/j.bmc.2008.07.054

  日期：2008.9

  Series of curcumin derivatives were synthesized; the inhibitory activities on thioredoxin reductase (TrxR) of all analogues were evaluated by DTNB assay in vitro. It is found that most of the analogues can inhibit TrxR in the low micromolar range; Structure-activity relationship analysis reveals that analogues with furan moiety have excellent inhibitory effect on TrxR in an irreversible manner, indicating that the furan moiety may serve as a possible pharmacophore during the interaction of curcumin analogues with TrxR. The effect of selected curcuminoids on growth of different TrxR overexpressed cancer cell lines was also investigated and discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and Identification of New 4-Arylidene Curcumin Analogues as Potential Anticancer Agents Targeting Nuclear Factor-κB Signaling Pathway
  作者：Xu Qiu、Yuhong Du、Bin Lou、Yinglin Zuo、Weiyan Shao、Yingpeng Huo、Jianing Huang、Yanjun Yu、Binhua Zhou、Jun Du、Haian Fu、Xianzhang Bu

  DOI：10.1021/jm1004545

  日期：2010.12.9

  A series of curcumin analogues including new 4-arylidene curcumin analogues (4-arylidene-1,7-bisarylhepta-1,6-diene-3,5-diones) were synthesized. Cell growth inhibition assays revealed that most 4-arylidene curcumin analogues can effectively decrease the growth of a panel of lung cancer cells at submicromolar and low micromolar concentrations. High content analysis technology coupled with biochemical studies showed that this new class of 4-arylidene curcumin analogues exhibits significantly improved NF-kappa B inhibition activity over the parent compound curcumin, at least in part by inhibiting I kappa B phosphorylation and degradation via IKK blockage; selected 4-arylidene curcumin analogues also reduced the tumorigenic potential of cancer cells in a clonogenic assay.