(1E,4Z,6E)-5-hydroxy-1,7-bis(4-methoxyphenyl)hepta-1,4,6-trien-3-one | 929110-66-7

• 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,4Z,6E)-5-hydroxy-1,7-bis(4-methoxyphenyl)hepta-1,4,6-trien-3-one
• CAS: 929110-66-7
• 化学式: C₂₁H₂₀O₄
• 分子量: 336.387
• InChiKey: UOIUXHFXWVZDEI-WTJGCYTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1E,4Z,6E)-5-hydroxy-1,7-bis(4-methoxyphenyl)hepta-1,4,6-trien-3-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 以90%的产率得到C₂₁H₂₄O₄
  参考文献：
  名称：

  A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids

  摘要：

  Several curcuminoids and tetrahydrocurcuminoids (THCs), bearing various hydroxyl and/or methoxy groups on their benzene rings, have been synthesized to study their antioxidant and hydrogen donating capacities using the DPPH method at 25 degrees C in methanol. The results show that the tetrahydrocurcuminoids are in general much more efficient than their curcuminoid analogs if they include a phenol group in meta- or para-position of the linking chain and a neighboring phenol or methoxy group. This efficiency gain of THCs by comparison to curcuminoids was attributed to the presence of benzylic hydrogens involved in the oxidation process of these compounds and not to the beta-diketone moiety in the chain. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.085
• 作为产物：
  描述：

  (1E,6E)-1,7-bis(4-methoxyphenyl)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(4-methoxyphenyl)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

• Mechanochemical synthesis of 2,2-difluoro-4, 6-bis(β-styryl)-1,3,2-dioxaborines and their use in cyanide ion sensing
  作者：Daisy R. Sherin、Sherin G. Thomas、Kallikat N. Rajasekharan

  DOI：10.1515/hc-2015-0096

  日期：2015.12.1

  The conversion of arylaldehydes to 1,7-diaryl-5-hydroxyhepta-1,4,6-trien-3-ones (curcuminoids) and the mechanochemical cyclization of these products to 2,2-difluoro-4,6-bis(β-styryl)-1,3,2-dioxaborines using BF₃-Et₂O are described. Investigation of the cyanide ion sensing ability of the 2,2-difluoro-4,6-bis(β-styryl)-1,3,2-dioxaborines, in relation to the substituent groups on the aryl ring, showed that a hydroxy susbstituent is required, preferably para to the intervening carbon bridge.

  摘要：将芳基醛转化为1,7-二芳基-5-羟基庚烷-1,4,6-三烯-3-酮（姜黄素类化合物），并描述了利用BF₃-Et₂O进行这些产物的机械化学环化反应，制备2,2-二氟-4,6-双(β-苯乙烯基)-1,3,2-二氧硼杂环。研究了2,2-二氟-4,6-双(β-苯乙烯基)-1,3,2-二氧硼杂环对氰离子的感应能力，发现与芳基环上的取代基团相关，需要一个羟基取代基，最好是位于介入碳桥的para位置。
• Synthesis and Photophysical Properties of Difluoroboron Complexes of Curcuminoid Derivatives Bearing Different Terminal Aromatic Units and a <i>meso</i>-Aryl Ring
  作者：Abdellah Felouat、Anthony D’Aléo、Fredéric Fages

  DOI：10.1021/jo400389h

  日期：2013.5.3

  of the nine compounds were investigated in solvents of different polarity. Meso-substitution with a phenyl ring has little influence on fluorescence emission properties in solution, radiative and nonradiative kinetic constants being similar for meso- and nonsubstituted compounds, which is in contrast to the case of BODIPY derivatives. However, introduction of an electron donor p-methoxy group at the

  描述了九种姜黄素及其二氟硼配合物的合成，其中七种含有内消旋-苯环。动态19 F NMR证实了以下事实：在室温下，后者的系统中该内-芳基片段的旋转受到限制，并且在更高的温度（> 45°C）下变得允许。处于固态的内消旋取代的衍生物的分子结构表明，相对于平均姜黄素平面，苯环位于高度扭曲的平面中。在不同极性的溶剂中研究了这九种化合物的光物理性质。中观用苯环取代对溶液中的荧光发射特性影响很小，内消旋和非取代化合物的辐射和非辐射动力学常数相似，这与BODIPY衍生物的情况相反。然而，在内消旋-苯环上引入电子给体对-甲氧基导致了姜黄素类π-系统荧光发射的小扰动。我们还报告了内消旋苯基对聚集固体排放特性的影响。
• 一种人工合成姜黄素及其衍生物的方法
  申请人：杭州瑞树生化有限公司

  公开号：CN106748705B

  公开（公告）日：2020-05-05

  本发明公开一种人工合成姜黄素及其衍生物的方法。该方法以乙酰丙酮钙为乙酰丙酮供源，经与相应的苯甲醛衍生物进行克莱森‑施密特酯缩合反应并在脱水剂硼酸三正丁酯催化下脱水后得到产物中间体(Ⅰ)姜黄素钙盐；然后中间体(Ⅰ)经一锅法水解得粗品，粗品提纯后得到最终产物姜黄素及其衍生物。与乙酰丙酮硼酸络合物法相比，本发明使用乙酰丙酮钙可以使得反应过程中乙酰丙酮基活性位点更为精确、活化，从而减少副产物的生成，提高姜黄素及其衍生物的产率。
• Iodine Impregnated Nano Neutral Alumina as an Efficient Catalyst for One Pot Green Synthesis of Curcumin Analogues by Microwave Irradiation
  作者：S. Elavarasan、D. Bhakiaraj、B. Chellakili、T. Elavarasan、M. Gopalakrishnan

  DOI：10.2174/15701786113109990047

  日期：2014.2

  Sixteen substituted curcumin analogs are synthesized in one pot by iodine impregnated nano neutral alumina catalyst under microwave irradiation. This catalyst shows higher reactivity by which it offered the reaction with higher yields and less reaction time. The prepared catalyst was characterized by FE-SEM, EDX and BET isotherm surface area. Also, the synthesized products were characterized by FT-IR, 1H NMR, 13C NMR, mass and elemental analysis.

  通过微波辐照下碘负载的纳米中性氧化铝催化剂，一步合成了十六个取代的姜黄素类似物。该催化剂表现出更高的反应活性，为反应提供了更高的产率和更短的反应时间。制备的催化剂通过场发射扫描电子显微镜（FE-SEM）、能量色散X射线光谱（EDX）和比表面积（BET）等温曲线进行了表征。此外，合成的产物通过傅里叶变换红外光谱（FT-IR）、氢核磁共振（1H NMR）、碳核磁共振（13C NMR）、质谱和元素分析进行了表征。
• Versatility of the Curcumin Scaffold: Discovery of Potent and Balanced Dual BACE-1 and GSK-3β Inhibitors
  作者：Rita Maria Concetta Di Martino、Angela De Simone、Vincenza Andrisano、Paola Bisignano、Alessandra Bisi、Silvia Gobbi、Angela Rampa、Romana Fato、Christian Bergamini、Daniel I. Perez、Ana Martinez、Giovanni Bottegoni、Andrea Cavalli、Federica Belluti

  DOI：10.1021/acs.jmedchem.5b00894

  日期：2016.1.28

  multifactorial maladies such as Alzheimer’s disease (AD). The concurrent inhibition of the validated AD targets β-secretase (BACE-1) and glycogen synthase kinase-3β (GSK-3β) by attacking both β-amyloid and tau protein cascades has been identified as a promising AD therapeutic strategy. In our study, curcumin was identified as a lead compound for the simultaneous inhibition of both targets; therefore, synthetic

  作为解决诸如阿尔茨海默氏病（AD）等复杂和多因素疾病的有用工具，多目标方法已得到越来越多的接受。通过攻击β-淀粉样蛋白和tau蛋白级联反应，同时抑制经过验证的AD靶标β-分泌酶（BACE-1）和糖原合酶激酶-3β（GSK-3β）被认为是一种有前途的AD治疗策略。在我们的研究中，姜黄素被确定为同时抑制两个靶点的先导化合物。因此，合成努力致力于获得一个新的基于姜黄素的类似物的小图书馆，并获得了许多有效和平衡的双靶标抑制剂。特别地，2，6，和7作为具有神经保护潜力和脑通透性的有前途的候选药物出现的。值得注意的是，对于一些新的化合物的对称二酮和β酮-烯醇互变异构形式被有意分离并测试在体外，使我们深入了解用于BACE-1和GSK-3β抑制的关键要求。