4,4'-((1E,6E)-4-(hydroxymethylene)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) diacetate | 1257441-69-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4,4'-((1E,6E)-4-(hydroxymethylene)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) diacetate
• 英文别名: [4-[(1E,6E)-7-(4-acetyloxy-3-methoxyphenyl)-4-(hydroxymethylidene)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] acetate
• CAS: 1257441-69-2
• 化学式: C₂₆H₂₄O₉
• 分子量: 480.471
• InChiKey: DLTIBCHAKPFMTG-NXZHAISVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  curcumin 、 乙酸酐 、 原甲酸三乙酯 反应 5.0h， 以29%的产率得到4,4'-((1E,6E)-4-(hydroxymethylene)-3,5-dioxohepta-1,6-diene-1,7-diyl)bis(2-methoxy-4,1-phenylene) diacetate
  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 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.