2-(3-Tert-butyl-4-hydroxyphenyl)-3-hydroxychromen-4-one | 1017266-14-6

• 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: 2-(3-Tert-butyl-4-hydroxyphenyl)-3-hydroxychromen-4-one
• CAS: 1017266-14-6
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: ASMQYKRSPLMSJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4'-benzyloxy-3'-tert-butylflavonol 在 盐酸 、 溶剂黄146 作用下， 反应 2.0h， 以17%的产率得到2-(3-Tert-butyl-4-hydroxyphenyl)-3-hydroxychromen-4-one
  参考文献：
  名称：

  Understanding the Cardioprotective Effects of Flavonols: Discovery of Relaxant Flavonols without Antioxidant Activity

  摘要：

  3 ',4 '-Dihydroxyflavonol (DiOHF) is a cardioprotective flavonol that can reduce injury after myocardial ischemia and reperfusion and thus is a promising small molecule for the treatment of cardiovascular disease. Like all vasoactive flavonols reported to date, DiOHF is both relaxant and antioxidant, hindering investigation of the relative contribution of each activity for the prevention of reperfusion injury. This study investigates structure-activity relationships of variations at the 3 ' and 4 ' positions of the B ring of DiOHF and vasorelaxant and antioxidant activities. Relaxation of rat isolated aortic rings precontracted with KCl revealed that the most active flavonols were those with a 4 '-hydroxyl group, with the opening of potassium channels as a possible contributing mechanism. For the antioxidant activity, with the exception of DiOHF, none of the flavonols investigated were able to significantly scavenge superoxide radical, and none of the three most potent vasorelaxant flavonols could prevent oxidant-induced endothelial dysfunction. The discovery of single-acting vasorelaxant flavonols without antioxidant activity, in particular 4 '-hydroxy-3 '-methoxyflavonol, will assist in investigating the mechanism of flavonol-induced cardioprotection.

  DOI：

  10.1021/jm070352h