(E)-3-(3-Hydroxy-4-methoxy-phenyl)-1-(2-hydroxy-phenyl)-propenone | 1621-66-5

• 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-Hydroxy-4-methoxy-phenyl)-1-(2-hydroxy-phenyl)-propenone
• 英文别名: 2',3-Dihydroxy-4-methoxychalcone；(E)-3-(3-hydroxy-4-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 1621-66-5
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: PJIBSNKWGMAWBJ-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-1-(2-Hydroxy-phenyl)-3-[4-methoxy-3-(tetrahydro-pyran-3-yloxy)-phenyl]-propenone 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (E)-3-(3-Hydroxy-4-methoxy-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

• 13C nuclear magnetic resonance studies on 1,3-diphenylprop-2-enones
  作者：V. S. Parmar、Sunil Sharma、J. S. Rathore、Meenu Garg、Sandhya Gupta、Sunita Malhotra、V. K. Sharma、Suddham Singh、P. M. Boll

  DOI：10.1002/mrc.1260280516

  日期：1990.5

  The 13C NMR spectra of 48 differently substituted chalcones (1,3‐diphenylprop‐2 enones) have been recorded and the results are discussed. The data will be useful in the identification of new/natural chalcones.

  已经记录了 48 个不同取代的查耳酮（1,3-二苯基丙-2 烯酮）的 13C NMR 光谱并讨论了结果。该数据将有助于识别新的/天然查耳酮。
• Synthesis and biological evaluation of 2′-hydroxychalcone derivatives as AMPK activators
  作者：Duy Vu Nguyen、Chatchai Muanprasat、Suchada Kaewin、Kowit Hengphasatporn、Yasuteru Shigeta、Thanyada Rungrotmongkol、Warinthorn Chavasiri

  DOI：10.1016/j.bioorg.2023.107048

  日期：2024.2

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