2-(4-butoxyphenyl)-3-hydroxy-4H-chromen-4-one

• 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-(4-butoxyphenyl)-3-hydroxy-4H-chromen-4-one
• 英文别名: 2-(4-Butoxyphenyl)-3-hydroxychromen-4-one
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: PCRKICNJQPBZLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-butoxyphenyl)-3-hydroxy-4H-chromen-4-one 、 碘甲烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以26 %的产率得到2-(4-butoxyphenyl)-3-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  A Structure Activity Relationship Study of 3,4’-Dimethoxyflavone for ArlRS Inhibition in Staphylococcus aureus

  摘要：

  耐甲氧西林金黄色葡萄球菌（MRSA）引起的感染很难治疗，因为它们对许多  内酰胺类抗生素都有耐药性，而且毒性因子的排泄高度协调。其中一种方法是...

  DOI：

  10.1039/d3ob00123g
• 作为产物：
  描述：

  4-丁氧基苯甲醛 在 双氧水 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 2-(4-butoxyphenyl)-3-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  A Structure Activity Relationship Study of 3,4’-Dimethoxyflavone for ArlRS Inhibition in Staphylococcus aureus

  摘要：

  耐甲氧西林金黄色葡萄球菌（MRSA）引起的感染很难治疗，因为它们对许多  内酰胺类抗生素都有耐药性，而且毒性因子的排泄高度协调。其中一种方法是...

  DOI：

  10.1039/d3ob00123g

文献信息

• Effect of Flavonol Derivatives on the Carrageenin-Induced Paw Edema in the Rat and Inhibition of Cyclooxygenase-1 and 5-Lipoxygenasein Vitro
  作者：Andrea M. Sobottka、Wolfgang Werner、Gottfried Blaschke、Werner Kiefer、Ulrike Nowe、Gerd Dannhardt、Elfrides E. S. Schapoval、Eloir P. Schenkel、Gerhard K.E. Scriba

  DOI：10.1002/1521-4184(20007)333:7<205::aid-ardp205>3.0.co;2-y

  日期：2000.7

  Alkoxyflavonols were synthesized by the Algar-Flynn-Oyamada (AFO) cyclization of chalcones. Hydroxyflavonols were prepared by dealkylation of methoxyflavonols by refluxing in hydroiodic acid. The alkoxyflavonols 3-hydroxy-2-(2,3,4-trimethoxyphenyl)-4H-chromen-4-one (6), 2-(4-ethoxyphenyl)-3-hydroxy-4H-chromen-4-one (7), 2-(4-butoxyphenyl)-3-hydroxy-4H-chromen-4-one (10), and 2-(3-n-butoxyphenyl)-3-hydroxy-4H-chromen-4-one (11) as well as the trihydroxy derivative 3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one (18) displayed high anti-inflammatory activity in carrageenin-induced rat paw edema. Additionally, the inhibition of enzymes of the arachidonic acid cascade by the derivatives was investigated in vitro. In contrast to the natural compound quercetin, the compounds were more potent inhibiting cyclooxygenase-1 than 5-lipoxygenase except for 3-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one (5). No correlation between the anti-inflammatory activity in the rat paw edema test and the inhibition of 5-lipoxygenase or cyclooxygenase-1 could be observed. In conclusion, the present results suggest that other effects than inhibition of these enzymes of the arachidonic acid cascade are important for the anti-inflammatory activity of the investigated alkoxyflavonols.
• CN115572276
  申请人：——

  公开号：——

  公开（公告）日：——
• A Structure Activity Relationship Study of 3,4’-Dimethoxyflavone for ArlRS Inhibition in Staphylococcus aureus
  作者：Alexander Weig、Patrick O'Connor、Jakub M. Kwiecinski、Orry Marciano、Angelica Nunag、Andrew Guitierrez、Roberta Melander、Alexander Horswill、Christian Melander

  DOI：10.1039/d3ob00123g

  日期：——

  Infections caused by methicillin-resistant Staphylococcus aureus (MRSA) are difficult to treat due to their resistance to many -lactam antibiotics, and their highly coordinated excretion of virulence factors. One way in...

  耐甲氧西林金黄色葡萄球菌（MRSA）引起的感染很难治疗，因为它们对许多  内酰胺类抗生素都有耐药性，而且毒性因子的排泄高度协调。其中一种方法是...