2-hydroxy-3,4,6-trimethoxypropiophenone | 51379-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-3,4,6-trimethoxypropiophenone
• 英文别名: 2-Hydroxy-3,4,6-trimethoxypropiophenon；1-(2-hydroxy-3,4,6-trimethoxy-phenyl)-propan-1-one；1-(2-Hydroxy-3,4,6-trimethoxy-phenyl)-propan-1-on；1-(2-Hydroxy-3,4,6-trimethoxyphenyl)propan-1-one
• CAS: 51379-76-1
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: WEGIFAYABXLPGL-UHFFFAOYSA-N

物化性质

• 熔点：
  129–130°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3,4,6-trimethoxypropiophenone 在 palladium on activated charcoal 氢氧化钾 、 aluminum tri-bromide 、 potassium-<3,4-bis-benzyloxy benzoate> 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 10.67h， 生成 2-(3,4-Dihydroxy-phenyl)-5-hydroxy-7,8-dimethoxy-3-methyl-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
• 作为产物：
  描述：

  1-(2,3,4,6-tetramethoxyphenyl)propan-1-one 在 三氯化铝 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 2-hydroxy-3,4,6-trimethoxypropiophenone
  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

• Bargellini, Gazzetta Chimica Italiana, 1915, vol. 45 I, p. 87
  作者：Bargellini

  DOI：——

  日期：——
• Rizzi, George P., Synthetic Communications, 1983, vol. 13, # 14, p. 1173 - 1180
  作者：Rizzi, George P.

  DOI：——

  日期：——
• Jain, Niveta; Gambhir, Geetu; Krishnamurty, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 4, p. 278 - 283
  作者：Jain, Niveta、Gambhir, Geetu、Krishnamurty

  DOI：——

  日期：——
• 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：——
• RIZZI, G. P., SYNTH. COMMUN., 1983, 13, N 14, 1173-1179
  作者：RIZZI, G. P.

  DOI：——

  日期：——