2-(2,3-二羟基苯基)-5,7-二羟基苯并吡喃-4-酮 | 74805-70-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2-(2,3-二羟基苯基)-5,7-二羟基苯并吡喃-4-酮
• 中文别名: 2-脱氧-2,2-二氟-4,5-O-(1-甲基亚乙基)-L-苏-五酸,乙基酯
• 英文名称: 5,7,2',3'-tetrahydroxyflavone
• 英文别名: 2-(2,3-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• CAS: 74805-70-2
• 化学式: C₁₅H₁₀O₆
• 分子量: 286.241
• InChiKey: STAGATUVRDVEAT-UHFFFAOYSA-N

物化性质

• 熔点：
  191-192 °C
• 沸点：
  597.0±50.0 °C(Predicted)
• 密度：
  1.654±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 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：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 氢溴酸 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 丙酮 为溶剂， 反应 40.0h， 生成 2-(2,3-二羟基苯基)-5,7-二羟基苯并吡喃-4-酮
  参考文献：
  名称：

  Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors

  摘要：

  The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC₅₀ of 72 ± 2 nM and its 8-C-glucoside orientin with an IC₅₀ of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 Å resolution and quambalarine B at 2.5 Å resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.

  DOI：

  10.1016/j.ejmech.2020.112754

文献信息

• JPH0525041A
  申请人：——

  公开号：JPH0525041A

  公开（公告）日：1993-02-02
• US5414015A
  申请人：——

  公开号：US5414015A

  公开（公告）日：1995-05-09
• [EN] AGENT CONTAINING B-RING-SUBSTITUTED FLAVONOID DERIVATIVES FOR TREATING ARTHRITIS<br/>[FR] AGENT CONTENANT DES DÉRIVÉS DE FLAVONOÏDE À CYCLE B SUBSTITUÉ POUR LE TRAITEMENT DE L'ARTHRITE
  申请人：KNU INDUSTRY COOPERATION FOUND

  公开号：WO2012096494A2

  公开（公告）日：2012-07-19

  본 발명은 하기 일반식 (I) 로 표기되는 플라보노이드 유도체, 이의 약학적으로 허용 가능한 그의 염을 유효성분으로 함유하는 조성물 및 이의 용도에 관한 것으로, 보다 상세하게는 하기 일반식 (Ⅰ)로 표기되는 플라보노이드 유도체 또는 약학적으로 허용 가능한 이들의 염은 연골 구성물질 분해 억제, ECM 분해 억제 활성, 및 MMP-13 발현 억제 활성을 나타내며, 만성 관절염 유발 동물실험에서 관절파괴 억제 활성이 탁월하므로, 관절염의 예방 및 치료에 유용한 약학조성물 및 건강기능식품에 이용될 수 있다.
• Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors
  作者：Václav Zima、Kateřina Radilová、Milan Kožíšek、Carlos Berenguer Albiñana、Elena Karlukova、Jiří Brynda、Jindřich Fanfrlík、Miroslav Flieger、Jan Hodek、Jan Weber、Pavel Majer、Jan Konvalinka、Aleš Machara

  DOI：10.1016/j.ejmech.2020.112754

  日期：2020.12

  The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC₅₀ of 72 ± 2 nM and its 8-C-glucoside orientin with an IC₅₀ of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 Å resolution and quambalarine B at 2.5 Å resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.