Toluene-4-sulfonic acid 3-hydroxy-5,6-dimethoxy-2-octanoyl-phenyl ester | 134081-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Toluene-4-sulfonic acid 3-hydroxy-5,6-dimethoxy-2-octanoyl-phenyl ester
• 英文别名: 1-[6-Hydroxy-3,4-dimethoxy-2-(4-methylphenylsulfonyloxy)phenyl]-1-octanone；(5-hydroxy-2,3-dimethoxy-6-octanoylphenyl) 4-methylbenzenesulfonate
• CAS: 134081-87-1
• 化学式: C₂₃H₃₀O₇S
• 分子量: 450.553
• InChiKey: RZDHYBKWMXDHSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid 3-hydroxy-5,6-dimethoxy-2-octanoyl-phenyl ester 在 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 3.33h， 生成 1-(6-Hydroxy-2,3,4-trimethoxy-phenyl)-octan-1-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
• 作为产物：
  描述：

  Toluene-4-sulfonic acid 2,3,5-trimethoxy-6-octanoyl-phenyl ester 在 aluminum tri-bromide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以84%的产率得到Toluene-4-sulfonic acid 3-hydroxy-5,6-dimethoxy-2-octanoyl-phenyl ester
  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：——