3-(2-methylpropyl)-2,4,6-trihydroxyacetophenone | 916916-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-methylpropyl)-2,4,6-trihydroxyacetophenone
• 英文别名: 1-[2,4,6-Trihydroxy-3-(2-methylpropyl)phenyl]ethanone
• CAS: 916916-75-1
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: QJZMOYHYVIRDMS-UHFFFAOYSA-N

物化性质

• 沸点：
  368.0±42.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-methylpropyl)-2,4,6-trihydroxyacetophenone 在 氢氧化钾 、 sodium acetate 、 potassium carbonate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 44.0h， 生成 8-(2-methylpropyl)-5,7,4'-tris(methoxymethoxy)flavanone
  参考文献：
  名称：

  Subtle Side-Chain Modifications of the Hop Phytoestrogen 8-Prenylnaringenin Result in Distinct Agonist/Antagonist Activity Profiles for Estrogen Receptors α and β

  摘要：

  In search of therapeutic agents for estrogen-related pathologies, phytoestrogens are being extensively explored. In contrast to naringenin, 8-prenylnaringenin is a potent hop-derived estrogenic compound, highlighting the importance of the prenyl group for hormonal activity. We investigated the effects of substituting the prenyl group at C(8) with alkyl chains of varying lengths and branching patterns on estrogen receptor (ER) subtype ER alpha- and ER beta-binding affinities and transcriptional activities. In addition, features of the ligand-induced receptor conformations were explored using a set of specific ER-binding peptides. The new 8-alkylnaringenins were found to span an activity spectrum ranging from full agonism to partial agonism to antagonism. Most strikingly, 8-(2,2-dimethylpropyl) naringenin exhibited full agonist character on ERR, but pronounced antagonist character on ER beta. Knowledge on how ER-subtype-selective activities can be designed provides valuable information for future drug or tool compound discovery.

  DOI：

  10.1021/jm060692n
• 作为产物：
  描述：

  3-(2-methylpropyl)-2,4,6-trimethoxyacetophenone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到3-(2-methylpropyl)-2,4,6-trihydroxyacetophenone
  参考文献：
  名称：

  Subtle Side-Chain Modifications of the Hop Phytoestrogen 8-Prenylnaringenin Result in Distinct Agonist/Antagonist Activity Profiles for Estrogen Receptors α and β

  摘要：

  In search of therapeutic agents for estrogen-related pathologies, phytoestrogens are being extensively explored. In contrast to naringenin, 8-prenylnaringenin is a potent hop-derived estrogenic compound, highlighting the importance of the prenyl group for hormonal activity. We investigated the effects of substituting the prenyl group at C(8) with alkyl chains of varying lengths and branching patterns on estrogen receptor (ER) subtype ER alpha- and ER beta-binding affinities and transcriptional activities. In addition, features of the ligand-induced receptor conformations were explored using a set of specific ER-binding peptides. The new 8-alkylnaringenins were found to span an activity spectrum ranging from full agonism to partial agonism to antagonism. Most strikingly, 8-(2,2-dimethylpropyl) naringenin exhibited full agonist character on ERR, but pronounced antagonist character on ER beta. Knowledge on how ER-subtype-selective activities can be designed provides valuable information for future drug or tool compound discovery.

  DOI：

  10.1021/jm060692n