4'-tert-Butylflavonol | 724754-30-7

• 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: 4'-tert-Butylflavonol
• 英文别名: 2-(4-Tert-butylphenyl)-3-hydroxychromen-4-one
• CAS: 724754-30-7
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: QBZIVWLZEFUVKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4'-tert-Butylflavonol 、 亚磷酸二乙酯 在 三乙胺 作用下， 以 四氯化碳 为溶剂， 反应 24.33h， 以35%的产率得到(2-(4-(tert-butyl)phenyl)-4-oxo-4H-chromen-3-yl) diethyl phosphate
  参考文献：
  名称：

  新型磷酸化黄酮类衍生物的合成及抗菌活性

  摘要：

  图形摘要 摘要 基于活性片段的连接方法，我们设计并合成了 15 种含有类黄酮单元的新型膦酸酯衍生物。目标化合物通过1H NMR、13C NMR、13P NMR、ESI-MS、IR和元素分析进行​​表征。生物测定结果表明，部分化合物在浓度为 100 µg/mL 时对米黄单胞菌 (Xoo) 具有优异的抑制活性 (≥57.38%)，50% 有效浓度 (EC50) 值范围为 40.29 至 66.87 µg/mL，优于商业抗菌剂双甲噻唑 (88.51 µg/mL)。化合物(2-(3-Bromophenyl)-4-oxo-4H-chromen-3-yl)二乙基膦酸酯(2f)和化合物(2-(4-(叔丁基)苯基)-4-oxo-4H-chromen) -3-yl) 膦酸二乙酯 (2h) 即使在 50 µg/mL 的浓度下也显示出更好的 Xoo 抑制率。此外，一些化合物对 Xanhomonas axonopodis

  DOI：

  10.1080/10426507.2017.1295963
• 作为产物：
  描述：

  4-tert-butyl-2'-hydroxychalcone 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 为溶剂， 以62%的产率得到4'-tert-Butylflavonol
  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

文献信息

• A flavonol-derived fluorescent probe for highly specific and sensitive detection of hydrazine in actual environmental samples and living zebrafish
  作者：Yu Wang、Qi Yan、Zhonglong Wang、Haijun Xu

  DOI：10.1016/j.saa.2022.122132

  日期：2023.3
• CN115304572
  申请人：——

  公开号：——

  公开（公告）日：——
• Understanding the Cardioprotective Effects of Flavonols: Discovery of Relaxant Flavonols without Antioxidant Activity
  作者：Cheng Xue Qin、Xingqiang Chen、Richard A. Hughes、Spencer J. Williams、Owen L. Woodman

  DOI：10.1021/jm070352h

  日期：2008.3.1

  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.
• Synthesis and antibacterial activity of novel phosphorylated flavonoid derivatives
  作者：Minguo Huang、Xianghui Ruan、Qin Li、Juping Zhang、Xinmin Zhong、Xiaobing Wang、Yan Xie、Wei Xiao、Wei Xue

  DOI：10.1080/10426507.2017.1295963

  日期：2017.8.3

  ABSTRACT ABSTRACT Fifteen novel phosphonate derivatives containing a flavonoid unit were designed and synthesized, based on the connection method of active fragments. The target compounds were characterized by 1H NMR, 13C NMR, 13P NMR, ESI-MS, IR, and elemental analysis. Bioassay results indicated that some of the compounds possessed an excellent inhibition activity (≥57.38%) against Xanthomonas oryzae pv

  图形摘要 摘要 基于活性片段的连接方法，我们设计并合成了 15 种含有类黄酮单元的新型膦酸酯衍生物。目标化合物通过1H NMR、13C NMR、13P NMR、ESI-MS、IR和元素分析进行​​表征。生物测定结果表明，部分化合物在浓度为 100 µg/mL 时对米黄单胞菌 (Xoo) 具有优异的抑制活性 (≥57.38%)，50% 有效浓度 (EC50) 值范围为 40.29 至 66.87 µg/mL，优于商业抗菌剂双甲噻唑 (88.51 µg/mL)。化合物(2-(3-Bromophenyl)-4-oxo-4H-chromen-3-yl)二乙基膦酸酯(2f)和化合物(2-(4-(叔丁基)苯基)-4-oxo-4H-chromen) -3-yl) 膦酸二乙酯 (2h) 即使在 50 µg/mL 的浓度下也显示出更好的 Xoo 抑制率。此外，一些化合物对 Xanhomonas axonopodis