4-Hydroxy-3-((E)-3-naphthalen-2-yl-acryloyl)-benzoic acid

• 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: 4-Hydroxy-3-((E)-3-naphthalen-2-yl-acryloyl)-benzoic acid
• 英文别名: 4-hydroxy-3-[(E)-3-naphthalen-2-ylprop-2-enoyl]benzoic acid
• 化学式: C₂₀H₁₄O₄
• 分子量: 318.329
• InChiKey: LQNZXQSZCMFGFD-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2'-羟基苯乙酮-5'-羧酸 、 2-萘甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以87%的产率得到4-Hydroxy-3-((E)-3-naphthalen-2-yl-acryloyl)-benzoic acid
  参考文献：
  名称：

  Synthesis of carboxylated flavonoids as new leads for LTD4 antagonists

  摘要：

  A series of 3'- and 5'-carboxylated chalcones, 6- or 8-carboxylated flavones and 6-carboxylated flavanones, -flavanols and -flavans were prepared. The compounds were tested for their inhibitory activities against leukotriene D-4 (LTD(4)) induced contraction of guinea-pig ileum. A new and convenient synthetic route to 3-acetyl-2-hydroxybenzoic acid (1d), a key intermediate for the synthesis of 3'-carboxy-2'-hydroxychalcones and 8-carboxylated flavones, was developed. The activities of the tested compounds ranged from 0 to 63% inhibition at 10(-5) M drug concentration against a single challenge of 10(-8) M LTD(4). Several compounds were tested in a radioligand binding assay against [H-3]LTD(4) on guinea-pig lung membrane. The quinoline-containing chalcone 12 and flavone 17 were found to exhibit significant but weak affinities for LTD(4) receptors with pK(D)-values of 4.95 and 4.83, respectively, and are interesting lead structures for the development of rigid LTD(4) antagonists. In contrast, the rest of the compounds tested in the binding assay did not show significant displacement of the radioligand, implying that for these compounds the functional activity is probably not caused by competitive antagonism at the LTD(4) receptor. The exact mechanism of the relaxant activity remains unclear.

  DOI：

  10.1016/s0223-5234(97)89849-2

文献信息

• Synthesis of carboxylated flavonoids as new leads for LTD4 antagonists
  作者：ME Zwaagstra、H Timmerman、RS Abdoelgafoer、MQ Zhang

  DOI：10.1016/s0223-5234(97)89849-2

  日期：1996.1

  A series of 3'- and 5'-carboxylated chalcones, 6- or 8-carboxylated flavones and 6-carboxylated flavanones, -flavanols and -flavans were prepared. The compounds were tested for their inhibitory activities against leukotriene D-4 (LTD(4)) induced contraction of guinea-pig ileum. A new and convenient synthetic route to 3-acetyl-2-hydroxybenzoic acid (1d), a key intermediate for the synthesis of 3'-carboxy-2'-hydroxychalcones and 8-carboxylated flavones, was developed. The activities of the tested compounds ranged from 0 to 63% inhibition at 10(-5) M drug concentration against a single challenge of 10(-8) M LTD(4). Several compounds were tested in a radioligand binding assay against [H-3]LTD(4) on guinea-pig lung membrane. The quinoline-containing chalcone 12 and flavone 17 were found to exhibit significant but weak affinities for LTD(4) receptors with pK(D)-values of 4.95 and 4.83, respectively, and are interesting lead structures for the development of rigid LTD(4) antagonists. In contrast, the rest of the compounds tested in the binding assay did not show significant displacement of the radioligand, implying that for these compounds the functional activity is probably not caused by competitive antagonism at the LTD(4) receptor. The exact mechanism of the relaxant activity remains unclear.