(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one | 118267-80-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
• 英文别名: 2'-Hydroxy-2,4',6'-trimethoxychalcone
• CAS: 118267-80-4
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: KKTYCZKXENFEJP-CMDGGOBGSA-N

物化性质

• 熔点：
  171-173 °C
• 沸点：
  529.9±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one 在 吡啶 、 mercury(II) diacetate 作用下， 以68%的产率得到2',4,6-trimethoxyaurone
  参考文献：
  名称：

  Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity

  摘要：

  A series of 2'-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.002
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 、 邻甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  通过Algar-Flynn-Oyamada（AFO）反应合成5-取代的黄酮醇：机理上的意义

  摘要：

  本文中，我们报告了一种合成方法，该方法通过使用碳酸钠/过氧化氢，通过Algar-Flynn-Oyamada反应（AFO）对5-取代的黄酮醇进行了改进，具有中等至高收率的一系列5-取代的黄酮醇。阐明了AFO反应的机理。LCMS分析和原位1 H NMR分析表明，在碱性碱/过氧化物条件下，环氧化物参与了从查尔酮到黄酮醇和/或金酮的转化。

  DOI：

  10.1016/j.tet.2017.06.064

文献信息

• Synthesis of 2-Benzylidene-3(2<i>H</i>)-benzofuran-3-ones (Aurones) by Oxidation of 2′-Hydroxychalcones with Mercury(II) Acetate
  作者：Haruo Sekizaki

  DOI：10.1246/bcsj.61.1407

  日期：1988.4

  The reaction of 2′-hydroxychalcones with mercury(II) acetate in acetic acid gives predominantly 2-benzylidene-3(2H)-benzofuran-3-ones (aurones) in 28–62% yield accompanied by flavanones in 5–21% yield.

  2'-羟基查尔酮与乙酸汞 (II) 在乙酸中的反应主要产生 2-benzylidene-3(2H)-benzofuran-3-ones (aurones)，产率为 28-62%，黄烷酮产率为 5-21% .
• Synthesis of 5-subsituted flavonols via the Algar-Flynn-Oyamada (AFO) reaction: The mechanistic implication
  作者：Xianyan Shen、Qiang Zhou、Wei Xiong、Wenchen Pu、Wei Zhang、Guolin Zhang、Chun Wang

  DOI：10.1016/j.tet.2017.06.064

  日期：2017.8

  Herein, we report a synthetic method with improved selectivity for 5-substituted flavonols via the Algar-Flynn-Oyamada reaction (AFO), by using of sodium carbonate/hydrogen peroxide A series of 5-substituted flavonols was obtained with moderate to high yields. The mechanism of the AFO reaction was elucidated. LCMS analysis and in situ 1H NMR analysis indicated that the epoxide was involved in the transformation

  本文中，我们报告了一种合成方法，该方法通过使用碳酸钠/过氧化氢，通过Algar-Flynn-Oyamada反应（AFO）对5-取代的黄酮醇进行了改进，具有中等至高收率的一系列5-取代的黄酮醇。阐明了AFO反应的机理。LCMS分析和原位1 H NMR分析表明，在碱性碱/过氧化物条件下，环氧化物参与了从查尔酮到黄酮醇和/或金酮的转化。
• 人PCID2蛋白在制备或筛选抗肿瘤药物中的应用及具有抗肿瘤活性的化合物
  申请人：兰州大学第一医院

  公开号：CN112870363B

  公开（公告）日：2022-02-18

  本发明属于生物技术和基因治疗技术领域，具体涉及一种人PCID2蛋白在制备或筛选抗肿瘤药物中的应用及抗肿瘤化合物。本发明发现PCID2基因促进肿瘤细胞增殖、调控细胞周期，是调节肿瘤发生发展的关键分子，可作为制备或筛选抗肿瘤药物的靶点蛋白；同时本发明以人PCID2蛋白为靶点蛋白，通过分子对接技术筛选出了一类靶向PCID2蛋白的抗肿瘤化合物，所述化合物能够显著抑制肿瘤细胞增殖，促进肿瘤细胞凋亡。
• Mechanisms of action and structure-activity relationships of cytotoxic flavokawain derivatives
  作者：Charlotte Thieury、Nicolas Lebouvier、Rémy Le Guével、Yann Barguil、Gaëtan Herbette、Cyril Antheaume、Edouard Hnawia、Yoshinori Asakawa、Mohammed Nour、Thierry Guillaudeux

  DOI：10.1016/j.bmc.2017.01.049

  日期：2017.3

  22 Flavokawain derivatives (FKd) were obtained by one step syntheses in order to conduct a SAR study to understand the structural requirements for optimum and selective cytotoxicity. FKd and natural flavokawains A and B found into kava, a South Pacific traditional beverage, were evaluated against nine cancer and one healthy cell lines. The targeted cell cycle phases as well as the effects on the induction of apoptosis and cell cycle protein levels were investigated. Therapeutic improvements (more activity and selectivity) were achieved with FKd compared to natural flavokawains and notably with the 2',3,4',6'-tetramethoxychalcone (FKd 19). FKd induced a Gl/S arrest on p53 wild-type cells and an M arrest on p53 mutant-type, via the up-regulation of p21 and cyclin B1 proteins, followed by apoptosis. Moreover, FKd exhibited a 24 h-effect on Akt/mTor normal cells versus a 48 h-effect on Akt/mTor up-regulated cells. The SAR study resulted in the conclusion that trimethoxy A-ring allowed the best compromise between cytotoxicity and selectivity, as well as the substitution of the meta position on the B-ring and the use of halogens substituents. (C) 2017 Elsevier Ltd. All rights reserved.
• Efficient One‐Pot Synthesis of Hydroxyflavanones by Cyclization and<i>O</i>‐Demethylation of Methoxychalcones
  作者：Tao Liu、Huazhou Ying、Guan Lin、Yongzhou Hu

  DOI：10.1080/00397910801991465

  日期：2008.5

  An efficient one-pot method for the synthesis of hydroxyflavanones is described. Methoxychalcones are treated with 36% HBr to afford cyclization and regioselective O-demethylation products (2a-i) while cyclization and complete O-demethylation products (3a-e) are obtained in the presence of 45% HI.

表征谱图