7-羟基-6-甲氧基-3-苯基色烯-4-酮 | 75187-55-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 7-羟基-6-甲氧基-3-苯基色烯-4-酮
• 英文名称: 7-hydroxy-6-methoxy-isoflavone
• 英文别名: 7-hydroxy-6-methoxy-3-phenyl-4H-chromen-4-one；6-methoxy-7-hydroxyisoflavone；7-Hydroxy-6-methoxyisoflavone；7-hydroxy-6-methoxy-3-phenylchromen-4-one
• CAS: 75187-55-2
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: GQVNHXNTSMARSK-UHFFFAOYSA-N

物化性质

• 沸点：
  488.3±45.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

7-羟基-6-甲氧基异黄酮已知的人类代谢物包括(2S,3S,4S,5R)-3,4,5-三羟基-6-(6-甲氧基-4-氧代-3-苯基色烯-7-基)氧杂环己烷-2-羧酸。

7-Hydroxy-6-methoxyisoflavone has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(6-methoxy-4-oxo-3-phenylchromen-7-yl)oxyoxane-2-carboxylic acid.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  7-羟基-6-甲氧基-3-苯基色烯-4-酮 在 5%-palladium/activated carbon 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 以52%的产率得到7-hydroxy-6-methoxyisoflavane
  参考文献：
  名称：

  Synthesis of Various Kinds of Isoflavones, Isoflavanes, and Biphenyl-Ketones and Their 1,1-Diphenyl-2-picrylhydrazyl Radical-Scavenging Activities

  摘要：

  合成了四十八种异黄酮（8）、三十一种异黄烷（9）以及四十七种联苯酮（10, 10′），这些化合物是由十一种取代酚（11）和六种苯乙酸（12）合成的。其中，有七十五种化合物是新发现的。这些化合物的自由基清除活性在pH 6.0下使用1,1-二苯基-2-吡唑啉酮（DPPH）进行了评估。我们发现，在四十三种含有儿茶酚基的化合物中，三十九种在A环或B环上表现出与儿茶素相似的高活性（ED50=12—54 μM）。在这些情况下，它们结构的其他部分似乎对活性影响不大。许多6-或8-羟基异黄烷（9E—I）及其联苯酮衍生物（10E—H）也显示出高活性（ED50=<50 μM），而它们对应的异黄酮（8E—I）则完全没有活性。具有在C5位增加羟基（9D）或在C6位增加甲氧基（9J）的7-羟基异黄烷则展现出高活性（ED50=26—32 μM）。本研究表明，天然异黄酮通过在C6、C8或C3′位置的羟基化，或通过代谢或生物转化形成异黄烷（9）和/或联苯酮衍生物（10′），具有表现抗氧化活性的可能性。

  DOI：

  10.1248/cpb.57.346
• 作为产物：
  描述：

  2-氯-2',4'-二羟基-5'-甲氧基-苯乙酮 在 potassium carbonate 、 三苯基膦 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 7-羟基-6-甲氧基-3-苯基色烯-4-酮
  参考文献：
  名称：

  一种黄豆黄素的合成方法

  摘要：

  本发明属有机化学及药物合成技术领域，涉及一种黄豆黄素及其类似物的合成方法，所述黄豆黄素即6‑甲氧基‑4’，7‑二羟基异黄酮。本发明按下式所示合成路线，合成制得黄豆黄素即6‑甲氧基‑4’，7‑二羟基异黄酮及其类似物，本发明的合成路线收率高，操作简便，条件温和，适合于规模化制备。

  公开号：

  CN109422713A

文献信息

• Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches
  作者：Baojian Wu、Xiaoqiang Wang、Shuxing Zhang、Ming Hu

  DOI：10.1007/s11095-012-0666-z

  日期：2012.6

  Catalytic selectivity of human UGT1A9, an important membrane-bound enzyme catalyzing glucuronidation of xenobiotics, was determined experimentally using 145 phenolics and analyzed by 3D-QSAR methods. Catalytic efficiency of UGT1A9 was determined by kinetic profiling. Quantitative structure activity relationships were analyzed using CoMFA and CoMSIA techniques. Molecular alignment of substrate structures was made by superimposing the glucuronidation site and its adjacent aromatic ring to achieve maximal steric overlap. For a substrate with multiple active glucuronidation sites, each site was considered a separate substrate. 3D-QSAR analyses produced statistically reliable models with good predictive power (CoMFA: q2 = 0.548, r2 = 0.949, r pred 2  = 0.775; CoMSIA: q2 = 0.579, r2 = 0.876, r pred 2  = 0.700). Contour coefficient maps were applied to elucidate structural features among substrates that are responsible for selectivity differences. Contour coefficient maps were overlaid in the catalytic pocket of a homology model of UGT1A9, enabling identification of the UGT1A9 catalytic pocket with a high degree of confidence. CoMFA/CoMSIA models can predict substrate selectivity and in vitro clearance of UGT1A9. Our findings also provide a possible molecular basis for understanding UGT1A9 functions and substrate selectivity.

  通过实验使用145种酚类化合物，并通过3D-QSAR方法分析，确定了人UGT1A9的催化选择性。UGT1A9是一种重要的膜结合酶，催化外源性物质的葡糖醛酸化反应。通过动力学分析确定了UGT1A9的催化效率。使用CoMFA和CoMSIA技术分析了定量结构活性关系。通过将葡糖醛酸化位点及其相邻的芳香环重叠，实现了底物结构的最大立体重叠。对于具有多个活性葡糖醛酸化位点的底物，每个位点被视为单独的底物。3D-QSAR分析产生了统计上可靠的模型，具有良好的预测能力（CoMFA：q2=0.548，r2=0.949，r pred 2=0.775；CoMSIA：q2=0.579，r2=0.876，r pred 2=0.700）。通过轮廓系数图阐明了底物中负责选择性差异的结构特征。将轮廓系数图叠加在UGT1A9的同源模型的催化口袋中，能够高度自信地识别UGT1A9的催化口袋。CoMFA/CoMSIA模型可以预测底物的选择性和UGT1A9的体外清除率。我们的发现还提供了理解UGT1A9功能和底物选择性的可能分子基础。
• Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
  作者：Jianzhuang Miao、Huaqing Cui、Jing Jin、Fangfang Lai、Hui Wen、Xiang Zhang、Gian Filippo Ruda、Xiaoguang Chen、Dali Yin

  DOI：10.1039/c4cc06762b

  日期：——

  A new class of fluorophores 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) is developed and is suitable as reagents for biological imaging.

  一种新型荧光物质3-烷基-6-甲氧基-7-羟基-香豆素（AMHCs）已开发，并适用于生物成像试剂。
• Compounds exhibiting efflux inhibitor activity and composition and uses thereof
  申请人：Wempe Fitzpatrick Michael

  公开号：US20070254859A1

  公开（公告）日：2007-11-01

  At least one compound chosen from compounds of Formula I: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, and mixtures of any of the foregoing, wherein: n is a number from 1 to 900, wherein the individual units may be the same or different; W is chosen from alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; each of R 2 , R 3 , R 4 and R 5 is independently chosen from —H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; Z′ is chosen from —O—, —N—, —NO—, —NR 4 —, —S—, —SO— and —SO 2 —, wherein R 4 is defined as above; each of X, X′, Y and Z is independently chosen from —CR 4 R 5 —, —NH—, —NR 4 —, —NO—, —O—, —NOR 4 —, —S—, —SO—, —SO 2 —, wherein R 4 and R 5 are defined as above; R 1 is chosen from a tocopherol, a steroid and a flavonoid; and R 6 is chosen from any R 1 , alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.