2-(3,4-Dihydroxy-phenyl)-5-hydroxy-6,7-dimethoxy-3-octyl-chromen-4-one | 134081-50-8

• 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-(3,4-Dihydroxy-phenyl)-5-hydroxy-6,7-dimethoxy-3-octyl-chromen-4-one
• 英文别名: 2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-3-octylchromen-4-one
• CAS: 134081-50-8
• 化学式: C₂₅H₃₀O₇
• 分子量: 442.509
• InChiKey: FVIZKUBRULQSFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  癸酰氯 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 三氯化铝 、 aluminum tri-bromide 、 potassium-<3,4-bis-benzyloxy benzoate> 、 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 18.5h， 生成 2-(3,4-Dihydroxy-phenyl)-5-hydroxy-6,7-dimethoxy-3-octyl-chromen-4-one
  参考文献：
  名称：

  Syntheses of 5,7,8- and 5,6,7-trioxygenated 3-alkyl-3',4'-dihydroxyflavones and their inhibitory activities against arachidonate 5-lipoxygenase

  摘要：

  5,6,7- and 5,7,8-Trioxygenated 3',4'-dihydroxyflavones were derivatized by introducing alkyl groups of various chain lengths at the 3-position of the flavone skeleton. These compounds were tested as inhibitors for arachidonate 5-lipoxygenase purified from porcine leukocytes. Modification of the 3-position with an alkyl group of 6-10 carbons markedly decreased the IC50 values. 3-Hexyl-3',4'-dihydroxy-5,7,8-trimethoxyflavone inhibited 5-lipoxygenase with an IC50 value of 58 nM. The platelet and leukocyte 12-lipoxygenases, 15-lipoxygenase of reticulocytes, and cyclooxygenase of vesicular gland were inhibited less potently (IC50 = 0.4, 0.4, 2.7, and 30-mu-M). Thus, the compound was a relatively selective inhibitor for 5-lipoxygenase.

  DOI：

  10.1021/jm00111a037

文献信息

• HORIE, TOKUNARU;TOMINAGA, HIDEAKI;KAWAMURA, YASUHIKO;HADA, TAKAHIKO;UEDA,+, J. MED. CHEM., 34,(1991) N, C. 2169-2176
  作者：HORIE, TOKUNARU、TOMINAGA, HIDEAKI、KAWAMURA, YASUHIKO、HADA, TAKAHIKO、UEDA,+

  DOI：——

  日期：——
• Syntheses of 5,7,8- and 5,6,7-trioxygenated 3-alkyl-3',4'-dihydroxyflavones and their inhibitory activities against arachidonate 5-lipoxygenase
  作者：Tokunaru Horie、Hideaki Tominaga、Yasuhiko Kawamura、Takahiko Hada、Natsuo Ueda、Yumi Amano、Shozo Yamamoto

  DOI：10.1021/jm00111a037

  日期：1991.7

  5,6,7- and 5,7,8-Trioxygenated 3',4'-dihydroxyflavones were derivatized by introducing alkyl groups of various chain lengths at the 3-position of the flavone skeleton. These compounds were tested as inhibitors for arachidonate 5-lipoxygenase purified from porcine leukocytes. Modification of the 3-position with an alkyl group of 6-10 carbons markedly decreased the IC50 values. 3-Hexyl-3',4'-dihydroxy-5,7,8-trimethoxyflavone inhibited 5-lipoxygenase with an IC50 value of 58 nM. The platelet and leukocyte 12-lipoxygenases, 15-lipoxygenase of reticulocytes, and cyclooxygenase of vesicular gland were inhibited less potently (IC50 = 0.4, 0.4, 2.7, and 30-mu-M). Thus, the compound was a relatively selective inhibitor for 5-lipoxygenase.