1,7-bis(2-methoxyphenyl)-1,6-heptadiene-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: 1,7-bis(2-methoxyphenyl)-1,6-heptadiene-3,5-dione
• 英文别名: (1E,6E)-1,7-bis(2-methoxyphenyl)hepta-1,6-diene-3,5-dione
• 化学式: C₂₁H₂₀O₄
• 分子量: 336.387
• InChiKey: QAPUBEVAKIWUPS-PHEQNACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,7-bis(2-methoxyphenyl)-1,6-heptadiene-3,5-dione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以88%的产率得到1,7-bis(2-hydroxyphenyl)-1,6-heptadiene-3,5-dione
  参考文献：
  名称：

  Structure activity relationship study of curcumin analogues toward the amyloid-beta aggregation inhibitor

  摘要：

  Inhibition of the amyloid beta aggregation process could possibly prevent the onset of Alzheimer's disease. In this article, we report a structure-activity relationship study of curcumin analogues for anti amyloid beta aggregation activity. Compound 7, the ideal amyloid beta aggregation inhibitor in vitro among synthesized curcumin analogues, has not only potent anti amyloid beta aggregation effects, but also water solubility more than 160 times that of curcumin. In addition, new approaches to improve water solubility of curcumin-type compounds are proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.076
• 作为产物：
  描述：

  水杨醛 在 boron trioxide 、 potassium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1,7-bis(2-methoxyphenyl)-1,6-heptadiene-3,5-dione
  参考文献：
  名称：

  Structure activity relationship study of curcumin analogues toward the amyloid-beta aggregation inhibitor

  摘要：

  Inhibition of the amyloid beta aggregation process could possibly prevent the onset of Alzheimer's disease. In this article, we report a structure-activity relationship study of curcumin analogues for anti amyloid beta aggregation activity. Compound 7, the ideal amyloid beta aggregation inhibitor in vitro among synthesized curcumin analogues, has not only potent anti amyloid beta aggregation effects, but also water solubility more than 160 times that of curcumin. In addition, new approaches to improve water solubility of curcumin-type compounds are proposed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.076

文献信息

• Anti-oxidant activities of curcumin and related enones
  作者：Waylon M. Weber、Lucy A. Hunsaker、Steve F. Abcouwer、Lorraine M. Deck、David L. Vander Jagt

  DOI：10.1016/j.bmc.2005.03.035

  日期：2005.6

  anti-oxidant properties. There are conflicting reports concerning the structural/electronic basis of the anti-oxidant activity of curcumin. Curcumin is a symmetrical diphenolic dienone. A series of enone analogues of curcumin were synthesized that included: (1) curcumin analogues that retained the 7-carbon spacer between the aryl rings; (2) curcumin analogues with a 5-carbon spacer; and (3) curcumin

  从香料姜黄获得的天然产物姜黄素（二氟甲酰甲烷，1,7-双（4-羟基-3-甲氧基苯基）-1,6-庚二烯-3,5-二酮）具有多种生物活性，包括抗癌，抗炎和抗血管生成活性。这些生物活性中的一些可能源自其抗氧化特性。关于姜黄素抗氧化活性的结构/电子基础的报道相互矛盾。姜黄素是对称的二酚二烯酮。合成了一系列姜黄素的烯酮类似物，包括：（1）保留在芳基环之间的7-碳间隔基的姜黄素类似物；（2）具有5碳间隔基的姜黄素类似物; （3）具有3个碳间隔基的姜黄素类似物（查耳酮）。这些系列包括保留或不包含酚基的成员。通过TRAP测定法和FRAP测定法测定抗氧化活性。大多数具有抗氧化活性的类似物保留了类似于姜黄素的酚环取代基。但是，许多没有酚取代基的类似物也是有活性的。这些非酚类类似物能够形成稳定的以碳为中心的叔基。
• Enamine-Mediated 1,3-Dipolar Cycloaddition Reaction of Curcumin Derivatives with Azides: Direct Access to 1,4,5-Trisubstituted 1,2,3-Triazoles
  作者：Wenjun Li、Zhenyan Shi

  DOI：10.1055/s-0036-1588385

  日期：——

  enamine-mediated [3+2] organocatalytic 1,3-dipolar cy­cloaddition reaction of curcumin derivatives with azides has been developed. This strategy could generate 1,4,5-trisubstituted 1,2,3-triazoles in high yields and regioselectivities under mild conditions. An enamine-mediated [3+2] organocatalytic 1,3-dipolar cy­cloaddition reaction of curcumin derivatives with azides has been developed. This strategy

  摘要 已经开发了姜黄素衍生物与叠氮化物的烯胺介导的[3 + 2]有机催化1,3-偶极环加成反应。该策略可以在温和条件下以高收率和区域选择性产生1,4,5-三取代的1,2,3-三唑。 已经开发了姜黄素衍生物与叠氮化物的烯胺介导的[3 + 2]有机催化1,3-偶极环加成反应。该策略可以在温和条件下以高收率和区域选择性产生1,4,5-三取代的1,2,3-三唑。
• Tubulin-Binding 3,5-Bis(styryl)pyrazoles as Lead Compounds for the Treatment of Castration-Resistant Prostate Cancer
  作者：Vivian W.Y. Liao、Anuradha Kumari、Rajeshwar Narlawar、Soma Vignarajan、David E. Hibbs、Dulal Panda、Paul W. Groundwater

  DOI：10.1124/mol.119.118539

  日期：2020.6

  resulting from their poor absorption, poor solubility, high first-pass metabolism, and efficient efflux by P-glycoprotein. New chemical entities for the treatment of prostate cancer are thus required, and we report here the synthesis and investigation of the mechanism of action of some bis(styryl)pyrazoles, demonstrating their potential as lead compounds for the treatment of prostate cancer.

  微管结合紫杉烷类，多西他赛和卡巴他赛通过静脉内给药治疗去势抵抗性前列腺癌（CRPC），因为这些药物的低和高度可变的生物利用度极大地阻碍了这些药物的口服给药。使用简单，快速且环保的微波辅助方案，我们合成了许多3,5-双（苯乙烯基）吡唑2a-1，因此可以筛选它们在不依赖雄激素的PC3前列腺癌细胞中的抗增殖活性。线。令人惊讶的是，这些结构简单的3,5-双（苯乙烯基）吡唑类化合物（2a和2l）中的两个在PC3细胞系的低微摩尔范围内具有50％的最大细胞增殖抑制（GI50）浓度，因此是选择用于进一步的生物学评估（细胞凋亡和细胞周期分析，以及对微管蛋白和微管的影响）。从这些研究中我们的发现表明，3,5-双[（1E）-2（2,6-二氯苯基）乙烯基] -1H-吡唑2l 1）对PC3细胞的细胞周期产生了显着影响，其中绝大多数G2 / M期的已处理细胞（89％）；2）即使去除了该化合物，仍会诱导PC3细胞死亡。3）与微管蛋白结合[解离常数（Kd）0
• Efficient synthesis of multicyclic spirooxindoles via a cascade Michael/Michael/oxa-Michael reaction of curcumins and isatylidene malononitriles
  作者：Xiao-Gang Yin、Xin-Yun Liu、Zhi-Peng Hu、Ming Yan

  DOI：10.1039/c2ob06995d

  日期：——

  A cascade Michael/Michael/oxa-Michael reaction between curcumins and isatylidene malononitriles has been developed. Multicyclic spirooxindoles were prepared in excellent yields and diastereoselectivities. DMAP was found to catalyze this transformation efficiently under mild reaction conditions.

  已开发出姜黄素和异亚甲基丙二腈之间的迈克尔/迈克尔/氧桥迈克尔级联反应。多环螺吲哚以优异的产率和立体选择性制备。DMAP在温和的反应条件下可有效催化这一转化。
• Cancer treatment using curcumin derivatives
  申请人：Vander Jagt L. David

  公开号：US20060276536A1

  公开（公告）日：2006-12-07

  Cancer or a precancerous condition is treated by administering a curcumin derivative to a subject.

  癌症或癌前病变可以通过向受试者施用姜黄素衍生物来治疗。