(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(3-methoxybenzylidene)hepta-1,6-diene-3,5-dione | 1257441-68-1

• 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: (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(3-methoxybenzylidene)hepta-1,6-diene-3,5-dione
• 英文别名: (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-[(3-methoxyphenyl)methylidene]hepta-1,6-diene-3,5-dione
• CAS: 1257441-68-1
• 化学式: C₂₉H₂₆O₇
• 分子量: 486.521
• InChiKey: JXIVJIZYMIRMKA-MKICQXMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  curcumin 、 3-甲氧基苯甲醛 在 吡啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 以59%的产率得到(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-(3-methoxybenzylidene)hepta-1,6-diene-3,5-dione
  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 Potential Antidiabetic Properties of Curcumin-Based Derivatives: An In Vitro and In Silico Study of α-Glucosidase and α-Amylase Inhibition
  作者：Hadi Adibi、Reza Khodarahmi、Mohammad Ezati、Fahimeh Ghavamipour、Narges Khosravi、Reza H. Sajedi、Maryam Chalabi、Alireza Farokhi

  DOI：10.2174/1573406418666220509101854

  日期：2023.1

  and α-amylase (α-Amy) are important enzymes in glucose metabolism. Diabetic control through the inhibition of carbohydrate hydrolyzing enzymes is established as an effective strategy. Methods: In this study, curcumin-based benzaldehyde derivatives with high stability, bioavailability, and favorable efficiency were synthesized. Results: The results showed that L13, L8, and L11 derivatives have the highest

  背景：在过去的二十年里，糖尿病作为最常见的代谢性疾病之一的流行已成为全球范围内的公共卫生问题。血糖控制对于延缓糖尿病相关并发症的发生和发展非常重要。α-糖苷酶（α-Glu）和α-淀粉酶（α-Amy）是葡萄糖代谢中的重要酶。通过抑制碳水化合物水解酶来控制糖尿病被确立为一种有效的策略。方法：在本研究中，合成了具有高稳定性、生物利用度和良好效率的姜黄素基苯甲醛衍生物。结果：结果表明，L13、L8 和 L11 衍生物对 α-Glu 的抑制作用最强，IC50 值分别为 18.65、20.6 和 31.7 μM，L11、L13、和L8衍生物对α-Amy的抑制作用最强，IC50值分别为14.8、21.8和44.9 μM。此外，还进行了酶抑制动力学表征，以了解酶抑制的机制。结论：与其他化合物相比，L13 对这两种酶均表现出可接受的抑制活性。考虑到合成化合物的抗氧化特性，L13 衍生物可能是进一步研究的合适
• 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.