3',4',5,7-tetrahydroxy-3-flavene | 1443134-18-6

• 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: 3',4',5,7-tetrahydroxy-3-flavene
• 英文别名: 4-(5,7-dihydroxy-2H-chromen-1-ium-2-yl)-2-hydroxyphenolate
• CAS: 1443134-18-6
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: MCOMSYCLUGORMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  木犀草素 在 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以51%的产率得到3',4',5,7-tetrahydroxy-3-flavene
  参考文献：
  名称：

  Synthesis, structure–activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors

  摘要：

  In a continuing study for discovering urease inhibitors based on flavonoids, nineteen reductive derivatives of flavonoids were synthesized and evaluated against Helicobacter pylori urease. Analysis of structure-activity relationship disclosed that 4-deoxy analogues are more potent than other reductive products. Out of them, 4',7,8-trihydroxyl-2-isoflavene (13) was found to be the most active with IC50 of 0.85 mu M, being over 20-fold more potent than the commercial available urease inhibitor, acetohydroxamic acid (AHA). Kinetics study revealed that 13 is a competitive inhibitor of H. pylori urease with a K-i value of 0.641 mu M, which is well matched with the results of molecular docking. Biological evaluation and mechanism study of 13 suggest that it is a good candidate for discovering novel anti-gastritis and anti-gastric ulcer agent. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.016

文献信息

• US9556140B2
  申请人：——

  公开号：US9556140B2

  公开（公告）日：2017-01-31
• Synthesis, structure–activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors
  作者：Zhu-Ping Xiao、Zhi-Yun Peng、Jing-Jun Dong、Juan He、Hui Ouyang、Yu-Ting Feng、Chun-Lei Lu、Wan-Qiang Lin、Jin-Xiang Wang、Yin-Ping Xiang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2013.03.016

  日期：2013.5

  In a continuing study for discovering urease inhibitors based on flavonoids, nineteen reductive derivatives of flavonoids were synthesized and evaluated against Helicobacter pylori urease. Analysis of structure-activity relationship disclosed that 4-deoxy analogues are more potent than other reductive products. Out of them, 4',7,8-trihydroxyl-2-isoflavene (13) was found to be the most active with IC50 of 0.85 mu M, being over 20-fold more potent than the commercial available urease inhibitor, acetohydroxamic acid (AHA). Kinetics study revealed that 13 is a competitive inhibitor of H. pylori urease with a K-i value of 0.641 mu M, which is well matched with the results of molecular docking. Biological evaluation and mechanism study of 13 suggest that it is a good candidate for discovering novel anti-gastritis and anti-gastric ulcer agent. (c) 2013 Elsevier Masson SAS. All rights reserved.