5-(3-acetyl-4-(pentyloxy)phenethyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one | 1357171-00-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 5-(3-acetyl-4-(pentyloxy)phenethyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
• CAS: 1357171-00-6
• 化学式: C₂₅H₃₀O₅
• 分子量: 410.51
• InChiKey: DKLCWIISFTYNKF-UHFFFAOYSA-N

物化性质

• 沸点：
  572.9±50.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.53
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(3-acetyl-4-(pentyloxy)phenethyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one 在 potassium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 以71%的产率得到2-(3-acetyl-4-(pentyloxy)phenethyl)-6-hydroxybenzoic acid
  参考文献：
  名称：

  6-alkylsalicylates are selective Tip60 inhibitors and target the acetyl-CoA binding site

  摘要：

  Histone acetyltransferases are important enzymes that regulate various cellular functions, such as epigenetic control of DNA transcription. Development of HAT inhibitors with high selectivity and potency will provide powerful mechanistic tools for the elucidation of the biological functions of HATs and may also have pharmacological value for potential new therapies. In this work, analogs of the known HAT inhibitor anacardic acid were synthesized and evaluated for inhibition of HAT activity. Biochemical assays revealed novel anacardic acid analogs that inhibited the human recombinant enzyme Tip60 selectively compared to PCAF and p300. Enzyme kinetics studies demonstrated that inhibition of Tip60 by one such novel anacardic acid derive, 20, was essentially competitive with Ac-CoA and non-competitive with the histone substrate. In addition, these HAT inhibitors effectively inhibited acetyltransferase activity of nuclear extracts on the histone H3 and H4 at micromolar concentrations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.001
• 作为产物：
  描述：

  1-(5-ethynyl-2-(pentyloxy)phenyl)ethanone 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 palladium 10% on activated carbon 、 氢气 、 二乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 40.0~100.0 ℃ 、303.99 kPa 条件下， 反应 0.5h， 生成 5-(3-acetyl-4-(pentyloxy)phenethyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
  参考文献：
  名称：

  6-alkylsalicylates are selective Tip60 inhibitors and target the acetyl-CoA binding site

  摘要：

  Histone acetyltransferases are important enzymes that regulate various cellular functions, such as epigenetic control of DNA transcription. Development of HAT inhibitors with high selectivity and potency will provide powerful mechanistic tools for the elucidation of the biological functions of HATs and may also have pharmacological value for potential new therapies. In this work, analogs of the known HAT inhibitor anacardic acid were synthesized and evaluated for inhibition of HAT activity. Biochemical assays revealed novel anacardic acid analogs that inhibited the human recombinant enzyme Tip60 selectively compared to PCAF and p300. Enzyme kinetics studies demonstrated that inhibition of Tip60 by one such novel anacardic acid derive, 20, was essentially competitive with Ac-CoA and non-competitive with the histone substrate. In addition, these HAT inhibitors effectively inhibited acetyltransferase activity of nuclear extracts on the histone H3 and H4 at micromolar concentrations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.001