3',4'-bis(benzyloxy)-3-(hexyloxy)-5,6,7-trimethoxyflavone | 134082-45-4

• 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: 3',4'-bis(benzyloxy)-3-(hexyloxy)-5,6,7-trimethoxyflavone
• 英文别名: 2-[3,4-bis(phenylmethoxy)phenyl]-3-hexoxy-5,6,7-trimethoxychromen-4-one
• CAS: 134082-45-4
• 化学式: C₃₈H₄₀O₈
• 分子量: 624.731
• InChiKey: UAUFBIYOHZHGQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3',4'-bis(benzyloxy)-3-(hexyloxy)-5,6,7-trimethoxyflavone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以56%的产率得到3-(hexyloxy)-5,6,7-trimethoxy-3',4'-dihydroxyflavone
  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
• 作为产物：
  描述：

  Toluene-4-sulfonic acid 2-(3,4-bis-benzyloxy-phenyl)-3-hexyloxy-6,7-dimethoxy-4-oxo-4H-chromen-5-yl ester 在 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 5.0h， 生成 3',4'-bis(benzyloxy)-3-(hexyloxy)-5,6,7-trimethoxyflavone
  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：——