3',4',5',5,6,7-hexahydroxyflavone | 68708-52-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3',4',5',5,6,7-hexahydroxyflavone
• 英文别名: 3',4',5,5',6,7-Hexahydroxyflavone；5,6,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
• CAS: 68708-52-1
• 化学式: C₁₅H₁₀O₈
• 分子量: 318.24
• InChiKey: PCOBUQBNVYZTBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  148
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3',4',5',5,6,7-hexahydroxyflavone 、 硫酸二甲酯 在 potassium carbonate 、 丙酮 作用下， 生成 3’,4’,5,5’,6,7-六甲氧基黄酮
  参考文献：
  名称：

  Rao et al., Proceedings - Indian Academy of Sciences, Section A, 1949, # 29, p. 72,75

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 硫酸 、 氢溴酸 、 双氧水 、 硼酸 、 potassium carbonate 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 85.17h， 生成 3',4',5',5,6,7-hexahydroxyflavone
  参考文献：
  名称：

  Importance of the B Ring and Its Substitution on the α-Glucosidase Inhibitory Activity of Baicalein, 5,6,7-Trihydroxyflavone

  摘要：

  为了评估黄芩素（5,6,7-三羟基黄酮，1）的 B 环对其强效α-葡萄糖苷酶抑制活性的贡献，我们制备了羟基色酮和 B 环取代的 5,6,7- 三羟基黄酮。缺乏 6-羟基取代的羟基色酮没有显示出任何抑制活性，而 5,6,7-三羟基-2-甲基色酮（5）则显示出较高的活性。在测试的 B 环取代的 5,6,7-三羟基黄酮中，4′-羟基、3′,4′-二羟基和 3′,4′,5′-三羟基取代的衍生物的活性高于 1。结果表明，1 的 B 环虽然对活性有利，但并不是必需的；5,6,7-三羟基黄酮 B 环上的羟基取代对活性有利，而甲氧基取代则不利；5,6,7-三羟基黄酮至少需要 4′-羟基取代才能提高活性，羟基的数量与活性无关。

  DOI：

  10.1271/bbb.68.1858

文献信息

• Redox‐Mediated Amination of Pyrogallol‐Based Polyphenols
  作者：Salavat S. Ashirbaev、Natércia F. Brás、Patricia Frei、Kuangjie Liu、Simone Moser、Hendrik Zipse

  DOI：10.1002/chem.202303783

  日期：2024.2.26

  Amyloids are known to be modified by natural polyphenols via amination. This study investigates the oxidative coupling mechanisms between polyphenols and N-nucleophiles, using in vitro and in silico approaches. It is shown that polyphenols with a pyrogallol substructure and an electron-withdrawing group at the C4a-position are most effective. These insights can play a crucial role in drug design against

  已知淀粉样蛋白可通过胺化作用被天然多酚修饰。本研究采用体外和计算机方法研究了多酚和N -亲核试剂之间的氧化偶联机制。结果表明，具有连苯三酚亚结构和 C4a 位吸电子基团的多酚最有效。这些见解可以在抗淀粉样蛋白生成的药物设计中发挥至关重要的作用。
• Balasubramanian et al., Journal Of Scientific and Industrial Research, 1955, vol. 14B, p. 6,10
  作者：Balasubramanian et al.

  DOI：——

  日期：——
• Studies of the selective O-alkylation and dealkylation of flavonoids. 13. An improved method for synthesizing 5,6,7-trihydroxyflavones from 6-hydroxy-5,7-dimethoxyflavones
  作者：Tokunaru Horie、Hideaki Tominaga、Yasuhiko Kawamura、Toshihide Yamada

  DOI：10.1021/jo00038a023

  日期：1992.6

  The demethylation of five 6-hydroxy-5,7-dimethoxyflavones 1 and their acetates with 30% w/v anhydrous aluminum chloride in acetonitrile was studied, and the following results were found. In the demethylation of 6-hydroxy-4',5,7-trimethoxyflavone (1a), 5,6-dihydroxy-4',7-dimethoxyflavone (2a) and 5,6,7-trihydroxy-4'-methoxyflavone (3a) were produced. Although the ratio of the two products varied according to the amount of aluminum chloride used, it became constant after 12-24 h because the cleavage of the 7-methoxy group in 2a was suppressed by iminoesterification of the 6-hydroxy group. In contrast, the demethylation of the 5- and 7-methoxy groups of acetate 4a proceeded smoothly by the process shown in Scheme II. The amount of 3a increased with increasing reaction time to give 3a as the main product after 36-48 h. The same phenomena were observed in the demethylation of the other 6-hydroxyflavones 1b-1e and their acetates 4b-4e. The demethylation of the acetates is widely applicable as a general method for synthesizing 5,6,7-trihydroxyflavones because the protection of hydroxy groups also suppresses the further cleavage of the methoxy group adjacent to the acetoxy group on the B ring of compounds such as 4d and 4e.
• JPS5392774A
  申请人：——

  公开号：JPS5392774A

  公开（公告）日：1978-08-15