5,6-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one | 1401320-18-0

• 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: 5,6-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 1401320-18-0
• 化学式: C₂₁H₂₀O₁₁
• 分子量: 448.383
• InChiKey: VUGRLRAUZWGZJP-STSJCENXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  野黄芩素 在 吡啶 、 喹啉 、 4-二甲氨基吡啶 、 silver(II) oxide 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 copper(II) sulfate 、 potassium iodide 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 54.0h， 生成 5,6-dihydroxy-2-(4-hydroxyphenyl)-7-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of glucose-containing scutellarein derivatives as neuroprotective agents based on metabolic mechanism of scutellarin in vivo

  摘要：

  Based on metabolic mechanism of scutellarin in vivo that scutellarin could be hydrolyzed into scutellarein by beta-glucuronide enzyme, some glucose-containing scutellarein derivatives were designed and synthesized through the introduction of glucose moiety at C-7 position of scutellarein via a glucosidic bond. Biological activity evaluation showed that these glucose-containing scutellarein derivatives exhibited potent DPPH radical scavenging activities. Furthermore, the improvement of physicochemical properties such as anticoagulant and neuroprotective activities alongside with the water solubility was achieved by introducing glucose. These findings suggest that the introduction of the glucose moiety to scutellarein wattants further development of this kind of compounds as neuroprotective agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.002

文献信息

• Design, synthesis and biological evaluation of glucose-containing scutellarein derivatives as neuroprotective agents based on metabolic mechanism of scutellarin in vivo
  作者：Nian-Guang Li、Min-Zhe Shen、Zhen-Jiang Wang、Yu-Ping Tang、Zhi-Hao Shi、Yi-Fan Fu、Qian-Ping Shi、Hao Tang、Jian-Ao Duan

  DOI：10.1016/j.bmcl.2012.11.002

  日期：2013.1

  Based on metabolic mechanism of scutellarin in vivo that scutellarin could be hydrolyzed into scutellarein by beta-glucuronide enzyme, some glucose-containing scutellarein derivatives were designed and synthesized through the introduction of glucose moiety at C-7 position of scutellarein via a glucosidic bond. Biological activity evaluation showed that these glucose-containing scutellarein derivatives exhibited potent DPPH radical scavenging activities. Furthermore, the improvement of physicochemical properties such as anticoagulant and neuroprotective activities alongside with the water solubility was achieved by introducing glucose. These findings suggest that the introduction of the glucose moiety to scutellarein wattants further development of this kind of compounds as neuroprotective agents. (C) 2012 Elsevier Ltd. All rights reserved.