6,7,4'-trihydroxy-8-(N,N-dimethylamino)methylflavone | 1104900-42-6

• 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: 6,7,4'-trihydroxy-8-(N,N-dimethylamino)methylflavone
• 英文别名: 8-[(Dimethylamino)methyl]-5,6,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one；8-[(dimethylamino)methyl]-5,6,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• CAS: 1104900-42-6
• 化学式: C₁₈H₁₇NO₆
• 分子量: 343.336
• InChiKey: BHQURWVVUKBNJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  红盏花素 在 氯化亚砜 、 sodium acetate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 101.0h， 生成 6,7,4'-trihydroxy-8-(N,N-dimethylamino)methylflavone
  参考文献：
  名称：

  Synthesis and biological evaluation of 8-substituted and deglucuronidated scutellarin and baicalin analogues as antioxidant responsive element activators

  摘要：

  黄酮类化合物是重要的生物活性膳食成分，已被证明是抗氧化反应元件（ARE）的激活剂，可以抵御电惊毒物和氧化应激。这些激活剂通过Nrf2因子诱导ARE基因转录，Nrf2是细胞保护基因的主要转录刺激因子，从Keap1复合物中释放出来。在本报告中，我们基于从两种常见中草药提取的黄酮类化合物——从登山花（Erigeron breviscapus (vant) Hand-Mazz）提取的scutellarin和从黄芩（Scutellaria baicalensis Georigi）提取的baicalin的结构，合成了几种8-取代和脱葡萄糖苷化的类似物，并鉴定了这些黄酮类化合物的ARE激活效果。我们发现，baicalin、脱葡萄糖苷化的baicalin和二氮杂环戊烯衍生物的活性较高。它们在剂量依赖性上上调ARE和NQO1的活性，并诱导Nrf2，得到了证实。结果表明，这三种类似物对ARE具有良好的上调效果，并且它们在进一步的神经保护测试中可能会被用于缓解氧化应激。

  DOI：

  10.1007/s11426-011-4361-4

文献信息

• Mannich bases of scutellarein as thrombin-inhibitors: Design, synthesis, biological activity and solubility
  作者：Nian-Guang Li、Shu-Lin Song、Min-Zhe Shen、Yu-Ping Tang、Zhi-Hao Shi、Hao Tang、Qian-Ping Shi、Yi-Fan Fu、Jian-Ao Duan

  DOI：10.1016/j.bmc.2012.10.015

  日期：2012.12

  Two series of 8-aminomethylated derivatives were prepared by Mannich reaction of scutellarein (2) with appropriate aliphatic amines, alicyclic amines and formaldehyde. All the compounds were tested for their thrombin inhibition activity through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT) and fibrinogen (FIB). The antioxidant activities of these target products were assessed by 1,1-diphenyl-2-picrylhydrazyl radical 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl (DPPH) assay using 3-(4,5)-dimethylthiahiazo (-z-y1)-3,5-di-phenytetrazoliumromide (MTT) assay method and the solubility were assessed by ultraviolet (UV). The results showed that morpholinyl aminomethylene substituent derivative (3d) demonstrated stronger anticoagulant activity, better water solubility and good antioxidant activity compared with scutellarein (2), which warrants further development as a agent for ischemic cerebrovascular disease treatment. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of 8-substituted and deglucuronidated scutellarin and baicalin analogues as antioxidant responsive element activators
  作者：Ping Yang、XiangZhen Kong、ChangMei Cheng、ChangYan Li、XiaoMing Yang、Xing’E Zhao

  DOI：10.1007/s11426-011-4361-4

  日期：2011.10

  Flavonoids are important bioactive dietary compounds, which are proved to be antioxidant responsive element (ARE) activators to defend against electrophilic toxicants and oxidative stress. The activators induce ARE gene transcription through Nrf2 factor, a major transcriptional stimulator of cytoprotective genes, relieved from a Keap1 complex. In this report, based on the structures of two flavonoids, scutellarin and baicalin, which are extracted from two common Chinese plants Dengzhanhua (Erigeron breviscapus (vant) Hand-Mazz) and Huangqin (Scutellaria baicalensis Georigi), respectively, we synthesized several 8-substituted and deglucuronidated analogues and identified the ARE activation effects of these flavonoids. We found that the Baicalin, deglucurnonidated Baicalin and diaza cyclopenta derivative were more active. Their dose-dependent upregulation activities of ARE and NQO1 and induction effects of Nrf2 were testified. The results presented that these three analogues had good upregulation effects on ARE, and they could be potentially utilized in relieving oxidative stress, upon further neuroprotective tests.

  黄酮类化合物是重要的生物活性膳食成分，已被证明是抗氧化反应元件（ARE）的激活剂，可以抵御电惊毒物和氧化应激。这些激活剂通过Nrf2因子诱导ARE基因转录，Nrf2是细胞保护基因的主要转录刺激因子，从Keap1复合物中释放出来。在本报告中，我们基于从两种常见中草药提取的黄酮类化合物——从登山花（Erigeron breviscapus (vant) Hand-Mazz）提取的scutellarin和从黄芩（Scutellaria baicalensis Georigi）提取的baicalin的结构，合成了几种8-取代和脱葡萄糖苷化的类似物，并鉴定了这些黄酮类化合物的ARE激活效果。我们发现，baicalin、脱葡萄糖苷化的baicalin和二氮杂环戊烯衍生物的活性较高。它们在剂量依赖性上上调ARE和NQO1的活性，并诱导Nrf2，得到了证实。结果表明，这三种类似物对ARE具有良好的上调效果，并且它们在进一步的神经保护测试中可能会被用于缓解氧化应激。