(E)-6-(3,4,5-trimethoxy phenyl)hex-5-ene-2,4-dione | 1257441-52-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-6-(3,4,5-trimethoxy phenyl)hex-5-ene-2,4-dione
• 英文别名: (E)-6-(3,4,5-trimethoxyphenyl)hex-5-ene-2,4-dione
• CAS: 1257441-52-3
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: ANQNPZDVRTYQNE-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-6-(3,4,5-trimethoxy phenyl)hex-5-ene-2,4-dione 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (5E)-6-(3,4,5-trihydroxyphenyl)hex-5-ene-2,4-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：

  没食子酸 在 lithium aluminium tetrahydride 、 重铬酸吡啶 、 硼酸三乙酯 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (E)-6-(3,4,5-trimethoxy phenyl)hex-5-ene-2,4-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

• Synthesis, screening and docking analysis of hispolon analogs as potential antitubercular agents
  作者：Neduri V. Balaji、Bollikolla Hari Babu、Gottumukkala V. Subbaraju、Kurre Purna Nagasree、Muthyala Murali Krishna Kumar

  DOI：10.1016/j.bmcl.2016.11.047

  日期：2017.1

  series of 20 hispolons/dihydrohispolons were synthesized and characterized by spectral data. These compounds were subjected to in vitro antitubercular activity screening against Mycobacterium tuberculosis (H37Rv) strain. The synthesized compounds showed varied antitubercular activity ranging from 100 to 1.6μg/mL. Among the screened compounds, four compounds (H1, H2, H3 and H15) have shown moderate activity

  合成了一系列的20个Hispolons / dihydrohispolons，并通过光谱数据对其进行了表征。对这些化合物进行了针对结核分枝杆菌（H37Rv）菌株的体外抗结核活性筛选。合成的化合物显示出从100到1.6μg/ mL的变化的抗结核活性。在筛选出的化合物中，四种化合物（H1，H2，H3和H15）具有中等活性，MIC为25μg/ mL。观察到二氢hispolon衍生物H14（MIC1.6μg/ mL），然后是H13（6.25μg/ mL）和H17（12.5μg/ mL），H19（3.125μg/ ML）的活性。对接模拟对测试化合物与β-酮酰基合酶（mtbFabH）之间可能的相互作用提供了很好的见解。药物-抑制剂组合研究显示，与针对霉菌酸生物合成的药物没有协同作用（异烟肼，
• X-ray crystal structures, density functional theory and docking on deacetylase enzyme for antiproliferative activity of hispolon derivatives on HCT116 colon cancer
  作者：Miriam Rossi、Francesco Caruso、Ilaria Costanzini、Carmen Kloer、Aron Sulovari、Elena Monti、Marzia Gariboldi、Emanuela Marras、Neduri V. Balaji、Modukuri V. Ramani、Gottumukkala V. Subbaraju

  DOI：10.1016/j.bmc.2019.07.008

  日期：2019.9

  them, SAHA (Vorinostat) is used in clinical studies. Investigations into possible mechanisms for hispolon derivatives active against the HCT116 colon tumor cell line are done after examining the structural results obtained from hispolon X-ray crystal structures as well as performing associated computational docking and Density Functional Theory techniques on HDAC6. These studies show preference for

  组蛋白衍生物对几种肿瘤细胞系的抗增殖作用强于相关姜黄素。组蛋白的大小小于姜黄素，比姜黄素更适合HDAC6的活性位点，HDAC6是一种赖氨酸残基的脱乙酰化酶。HDAC被认为是肿瘤药物发现的潜在靶标，而异羟肟酸酯是已知的HDAC抑制剂。其中之一，SAHA（Vorinostat）用于临床研究。在研究了从组蛋白X射线晶体结构获得的结构结果并在HDAC6上执行了相关的计算对接和密度泛函理论技术之后，对组蛋白衍生物对HCT116结肠肿瘤细胞系具有活性的可能机制进行了研究。这些研究表明，通过螯合Zn中心，人们更喜欢HDAC6活性位点，与其他无效的Hispolon衍生物相反，后者仅与金属中心建立单键。结构活性关系清楚地表明，组蛋白桥的氢化还导致单键（非螯合）组蛋白-Zn结合，并始终取消了对HCT116肿瘤的抗增殖作用。
• Synthesis, X-ray diffraction and anti-proliferative biological activity of hispolon derivatives and their (η6-p-cymene)(Hispolonato)Ruthenium[II] chloride complexes
  作者：Francesco Caruso、Gottumukkala V. Subbaraju、Modukuri V. Ramani、Marzia Gariboldi、Emanuela Marras、Carmen Kloer、Aron Sulovari、Sarjit Kaur、Miriam Rossi

  DOI：10.1016/j.ica.2022.121099

  日期：2022.11

  previously shown antitumor activity. In this study we present the synthesis, chemical characterization and in vitro anti-proliferative activity of three [(η6-p-cymene)Ru(L)Cl] neutral complexes, where L = hispolon derivatives. The single crystal X-ray structures of the three Ru complexes all have the expected piano stool geometry with the p-cymene ligand at the apex of the piano stool and occupying three of

  Hispolon 是从桑黄和桑黄真菌中提取的天然产物，此前已显示出抗肿瘤活性。在这项研究中，我们介绍了三种 [(η 6 - p -伞花烃)Ru(L)Cl] 中性配合物的合成、化学表征和体外抗增殖活性，其中 L = hispolon 衍生物。三种Ru配合物的单晶X射线结构都具有预期的钢琴凳几何形状，p-聚伞花烃配体位于钢琴凳的顶点，并以扭曲的八面体排列占据三个位置。完成八面体配位球的是去质子化hispolon衍生物的两个β-二酮氧原子，它们以双齿方式配位 和一个氯原子。研究了三种 hispolon 衍生物及其相应复合物对 A549 肺、HCT116 结肠和 U87 胶质母细胞瘤细胞系的细胞毒性。在胶质母细胞瘤细胞系中，生物活性增加（降低 IC 50) 在芳烃-钌络合后对所有三种 hispolon 均可见：2,3,4-三甲氧基-hisp8 (Hisp8) 高 5.1 倍，3-甲氧基,4-羟​​基-hisp1
• 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.