7-hydroxy-4'-methoxy-2-isoflavene | 1006614-54-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-hydroxy-4'-methoxy-2-isoflavene
• 英文别名: 3-(4-methoxyphenyl)-4H-chromen-7-ol
• CAS: 1006614-54-5
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: BWAUURSNSPNMMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  刺芒柄花素 在 sodium tetrahydroborate 、 乙醇 作用下， 以55%的产率得到7-hydroxy-4'-methoxy-2-isoflavene
  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

• Processes for Preparing Isoflavonoids using 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran as a Starting Material
  申请人：Wang Eng-Chi

  公开号：US20100298581A1

  公开（公告）日：2010-11-25

  Disclosed herein are processes for the preparation of isoflavonoids, in particular haginin E, equol, daidzein, formononetin and the like, in which 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran is used as a common starting material.

  本文披露了一种制备异黄酮类化合物的方法，特别是制备haginin E、equol、daidzein、formononetin等化合物的方法，其中7-苄氧基-3-(4-甲氧基苯基)-2H-1-苯并吡喁被用作共同的起始原料。
• US7875735B2
  申请人：——

  公开号：US7875735B2

  公开（公告）日：2011-01-25
• 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.