(E)-3-[3,4-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-1-(2-hydroxy-phenyl)-propenone | 130600-78-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-[3,4-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-1-(2-hydroxy-phenyl)-propenone
• CAS: 130600-78-1
• 化学式: C₂₅H₂₈O₆
• 分子量: 424.494
• InChiKey: VPIVIEXJHDWZOX-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-3-[3,4-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-1-(2-hydroxy-phenyl)-propenone 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 3,4,2'-trihydroxy-trans-chalcone
  参考文献：
  名称：

  3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors

  摘要：

  A novel series of 3,4-dihydroxychalcones was synthesized to evaluate their effects against 5-lipoxygenase and cyclooxygenase. Almost all compounds exhibited potent inhibitory effects on 5-lipoxygenase with antioxidative effects, and some also inhibited cyclooxygenase. The 2',5'-disubstituted 3,4-dihydroxychalcones with hydroxy or alkoxy groups exhibited optimal inhibition of cyclooxygenase. We found that 2',5'-dimethoxy-3,4-dihydroxychalcone (37; HX-0836) inhibited cyclooxygenase to the same degree as flufenamic acid and 6-lipoxygenase, more than quercetin. Finally, these active inhibitors of 5-lipoxygenase inhibited arachidonic acid-induced mouse ear edema more than phenidone.

  DOI：

  10.1021/jm00076a019
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 barium dihydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (E)-3-[3,4-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-1-(2-hydroxy-phenyl)-propenone
  参考文献：
  名称：

  3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors

  摘要：

  A novel series of 3,4-dihydroxychalcones was synthesized to evaluate their effects against 5-lipoxygenase and cyclooxygenase. Almost all compounds exhibited potent inhibitory effects on 5-lipoxygenase with antioxidative effects, and some also inhibited cyclooxygenase. The 2',5'-disubstituted 3,4-dihydroxychalcones with hydroxy or alkoxy groups exhibited optimal inhibition of cyclooxygenase. We found that 2',5'-dimethoxy-3,4-dihydroxychalcone (37; HX-0836) inhibited cyclooxygenase to the same degree as flufenamic acid and 6-lipoxygenase, more than quercetin. Finally, these active inhibitors of 5-lipoxygenase inhibited arachidonic acid-induced mouse ear edema more than phenidone.

  DOI：

  10.1021/jm00076a019

文献信息

• Chalcone derivatives and process for producing the same
  申请人：DAINIPPON INK AND CHEMICALS, INC.

  公开号：EP0370461B1

  公开（公告）日：1995-06-28