3-p-茴香酰刺槐黄素 | 874519-13-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 中文名称: 3-p-茴香酰刺槐黄素
• 英文名称: 5,7-dihydroxy-3-(4-methoxy-benzoyl)-2-(4-methoxy-phenyl)-chromen-4-one
• 英文别名: 5,7-Dihydroxy-3-(4-methoxy-benzoyl)-2-(4-methoxy-phenyl)-chromen-4-on；3-p-Anisoyl Acacetin；5,7-dihydroxy-3-(4-methoxybenzoyl)-2-(4-methoxyphenyl)chromen-4-one
• CAS: 874519-13-8
• 化学式: C₂₄H₁₈O₇
• 分子量: 418.403
• InChiKey: ORTUTEQLHXVWNO-UHFFFAOYSA-N

物化性质

• 沸点：
  645.5±55.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、二甲基亚砜、乙酸乙酯（少量）、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-p-茴香酰刺槐黄素 在 甲醇 、 氢氧化钾 、 三氯化铝 、 乙醇 、 硝基苯 、 2-溴丙酰溴 作用下， 生成 3-hydroxy-4-methoxy-7-(4-methoxy-phenyl)-2-methyl-furo[2,3-f]chromen-9-one
  参考文献：
  名称：

  Kogure, Nippon Kagaku Zasshi, 1952, vol. 73, p. 308

  摘要：

  DOI：
• 作为产物：
  描述：

  2',4',6'-tri(p-methoxybenzoyloxy)acetophenone 在 吡啶 、 硫酸 、 potassium carbonate 、 溶剂黄146 作用下， 反应 5.0h， 生成 3-p-茴香酰刺槐黄素
  参考文献：
  名称：

  3-Aroyl-5-hydroxyflavones: synthesis and mechanistic studies by mass spectrometry

  摘要：

  The synthesis and mass spectra of three 3-aroyl-5-hydroxyflavones are reported. The interpretation of the mechanistic pathways for the fragmentation of the metastable molecular ions of these compounds was achieved through the analysis of their mass-analysed ion kinetic energy (MIKE) spectra and of the B-2/E spectra of a few fragment ions. Labelling of the hydroxyl proton with deuterium and the analysis of the MIKE spectra of a model compound with chlorine atoms in the 2',6'- and 2 '',6 ''-positions led to a mechanism for the losses of OH. and HCO. which involves hydrogen migration from the 2 ''- or 6 ''-position to the 4-carbonyl oxygen atom. A mechanism for the loss of a neutral molecule of anisole from the molecular ion of the 3-aroyl-5-hydroxyflavone with a methoxyl group in the 4'- and 4 ''-positions is also suggested. For the flavones with hydrogen or chlorine substituents at these positions, loss of a phenyl (or chlorophenyl) radical occurs instead. (C) 1997 by John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1096-9888(199709)32:9<930::aid-jms549>3.0.co;2-e

文献信息

• Biological activity evaluation and molecular docking study of chromone derivatives as cyclooxygenase-2 inhibitors
  作者：Chirattikan Maicheen、Narumol Phosrithong、Jiraporn Ungwitayatorn

  DOI：10.1007/s00044-017-1786-0

  日期：2017.3

  A series of chromone derivatives have been evaluated as potential cyclooxygenase-2 (COX-2) inhibitors. The four most potent compounds, 48, 41, 39, and 35 displayed IC50 values of 3.30, 6.86, 7.36 and 7.46 µM, respectively. Compounds 35 and 38 showed higher selectivity for COX-2 (selectivity index, SI = 7.48 and 5.46, respectively) than celecoxib (SI = 4.17 in the same test) whereas compound 39 showed

  一系列色酮衍生物已被评估为潜在的环氧合酶2（COX-2）抑制剂。四个最有效的化合物，48，41，39，和35显示的IC 50个分别3.30，6.86，7.36和7.46μM的值，。与塞来昔布（同一试验中SI = 4.17）相比，化合物35和38对COX-2的选择性更高（分别为SI = 7.48和5.46），而化合物39对塞来昔布的选择性更高（SI = 4.19）。化合物的分子体积35（312.84埃3）和38（314.18埃3）类似于塞来考昔（299.28埃3），但大于布洛芬（211.83埃3）。在结合能和结合方式的评价方面，对接结果与实验生物学数据非常吻合。化合物35，38和39对COX-2具有更高的结合亲和力比COX-1（间-9.77和-11.42千卡/摩尔结合能）（-6.28和-7.88千卡/摩尔之间的结合能量）。这三种色酮化合物在与塞来昔布相同的方向上也显示出活性构象。因此，该系列
• Kogure; Kubota, Journal of the Institute of Polytechnics, Osaka City University, Series C: Chemistry, 1951, vol. <C> 2, p. 76,80
  作者：Kogure、Kubota

  DOI：——

  日期：——
• 905. Chelate systems. Part I
  作者：T. H. Simpson、Linda Garden

  DOI：10.1039/jr9520004638

  日期：——
• Kogure, Nippon Kagaku Zasshi, 1952, vol. 73, p. 308
  作者：Kogure

  DOI：——

  日期：——
• 3-Aroyl-5-hydroxyflavones: synthesis and mechanistic studies by mass spectrometry
  作者：Ana M. Cardoso、Artur M. S. Silva、Cristina M. F. Barros、Lúcia M. P. M. Almeida、A. J. Ferrer-Correia、José A. S. Cavaleiro

  DOI：10.1002/(sici)1096-9888(199709)32:9<930::aid-jms549>3.0.co;2-e

  日期：1997.9

  The synthesis and mass spectra of three 3-aroyl-5-hydroxyflavones are reported. The interpretation of the mechanistic pathways for the fragmentation of the metastable molecular ions of these compounds was achieved through the analysis of their mass-analysed ion kinetic energy (MIKE) spectra and of the B-2/E spectra of a few fragment ions. Labelling of the hydroxyl proton with deuterium and the analysis of the MIKE spectra of a model compound with chlorine atoms in the 2',6'- and 2 '',6 ''-positions led to a mechanism for the losses of OH. and HCO. which involves hydrogen migration from the 2 ''- or 6 ''-position to the 4-carbonyl oxygen atom. A mechanism for the loss of a neutral molecule of anisole from the molecular ion of the 3-aroyl-5-hydroxyflavone with a methoxyl group in the 4'- and 4 ''-positions is also suggested. For the flavones with hydrogen or chlorine substituents at these positions, loss of a phenyl (or chlorophenyl) radical occurs instead. (C) 1997 by John Wiley & Sons, Ltd.