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

• 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)-4-(4-hydroxy-3-methoxybenzylidene)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• 英文别名: 4-(4-hydroxy-3-methoxybenzylidene)curcumin；1t,7t-bis-(4-hydroxy-3-methoxy-phenyl)-4-vanillylidene-hepta-1,6-diene-3,5-dione；1t,7t-Bis-(4-hydroxy-3-methoxy-phenyl)-4-vanillyliden-hepta-1,6-dien-3,5-dion；4-(4-Hydroxy-3-methoxybenzylidene)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione；(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methylidene]hepta-1,6-diene-3,5-dione
• 化学式: C₂₉H₂₆O₈
• 分子量: 502.521
• InChiKey: UBAXBJGMRVTJRB-LUZURFALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 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：
  123
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  姜黄素 、 香草醛 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以43%的产率得到(1E,6E)-4-(4-hydroxy-3-methoxybenzylidene)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
  参考文献：
  名称：

  在分子拥挤条件下用姜黄素及其合成类似物靶向人类端粒G-四链体DNA †

  摘要：

  已经表明端粒G-四链体的形成抑制端粒酶活性。实际上，许多能够与G-tetrads进行π堆积的小分子已显示出通过稳定G-四链体来抑制端粒酶活性的能力。姜黄素具有广泛的医学特性，从抗菌，抗病毒，原生动物，真菌和抗炎活性到抗癌活性。我们已经研究了姜黄素及其结构类似物与人类端粒序列AG 3（T 2 AG 3）3在分子拥挤条件下的相互作用。实验研究表明存在AG 3（T 2 AG 3）3 /姜黄素复合物在分子拥挤条件下的结合亲和力为0.72×10 6 M -1。紫外可见吸收光谱，荧光TO位移测定，圆二色性和分子对接研究的结果表明，姜黄素及其类似物通过G与四联体DNA相互作用。凹槽装订。尽管此处研究的姜黄素的其他类似物以定性相似的方式与G-四链体结合，但与姜黄素相比，它们的亲和力相对较低。姜黄素的甲氧基-亚苄基衍生物Knoevenagel缩合物也显示出与G-四链体DNA的显着结合，尽管亲和力下降了两倍。

  DOI：

  10.1039/c5ra17390f

文献信息

• Targeting human telomeric G-quadruplex DNA with curcumin and its synthesized analogues under molecular crowding conditions
  作者：Niki S. Jha、Satyendra Mishra、Ashalatha S. Mamidi、Archita Mishra、Shailendra K. Jha、Avadhesha Surolia

  DOI：10.1039/c5ra17390f

  日期：——

  its structural analogues with the human telomeric sequence AG3(T2AG3)3 under molecular crowding conditions. Experimental studies indicated the existence of a AG3(T2AG3)3/curcumin complex with binding affinity of 0.72 × 106 M−1 under molecular crowding conditions. The results from UV-visible absorption spectroscopy, a fluorescent TO displacement assay, circular dichroism and molecular docking studies,

  已经表明端粒G-四链体的形成抑制端粒酶活性。实际上，许多能够与G-tetrads进行π堆积的小分子已显示出通过稳定G-四链体来抑制端粒酶活性的能力。姜黄素具有广泛的医学特性，从抗菌，抗病毒，原生动物，真菌和抗炎活性到抗癌活性。我们已经研究了姜黄素及其结构类似物与人类端粒序列AG 3（T 2 AG 3）3在分子拥挤条件下的相互作用。实验研究表明存在AG 3（T 2 AG 3）3 /姜黄素复合物在分子拥挤条件下的结合亲和力为0.72×10 6 M -1。紫外可见吸收光谱，荧光TO位移测定，圆二色性和分子对接研究的结果表明，姜黄素及其类似物通过G与四联体DNA相互作用。凹槽装订。尽管此处研究的姜黄素的其他类似物以定性相似的方式与G-四链体结合，但与姜黄素相比，它们的亲和力相对较低。姜黄素的甲氧基-亚苄基衍生物Knoevenagel缩合物也显示出与G-四链体DNA的显着结合，尽管亲和力下降了两倍。
• 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.
• Rebeiro et al., Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1950, vol. 19/3 A, p. 38,47, 50
  作者：Rebeiro et al.

  DOI：——

  日期：——
• Pavolini et al., Annali di Chimica, 1950, vol. 40, p. 280,289
  作者：Pavolini et al.

  DOI：——

  日期：——
• Synthesis and evaluation of antimicrobial activity of 4H-pyrimido[2,1-b]benzothiazole, pyrazole and benzylidene derivatives of curcumin
  作者：Pramod K. Sahu、Praveen K. Sahu、S.K. Gupta、D. Thavaselvam、D.D. Agarwal

  DOI：10.1016/j.ejmech.2012.05.020

  日期：2012.8

  A novel, one-pot, simple, efficient procedure for 4H-pyrimido[2,1-b]benzothiazole (4a-h), pyrazole (6a-d) and benzylidene (7a-d) derivatives of curcumin under solvent and solvent free conditions in microwave with good yield is have been synthesized. The synthesized compounds were evaluated for their antibacterial activity against gram-positive and gram-negative bacteria viz. Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella typhi, Escherichia coli, Bacillus cereus and Providencia rettgeri and antifungal activity against fungi viz Aspergillus niger, Aspergillus fumigates, Aspergillus flavus. Detailed mechanistic study shows reaction proceeds through Knoevenagel type intermediate 3a which has been suggested as key intermediate for reaction (Fig. 3). (C) 2012 Elsevier Masson SAS. All rights reserved.