Methyl 2-[(3-bromo-1,4-dimethoxynaphthalen-2-yl)methylidene]-4-methoxybutanoate | 1136840-08-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Methyl 2-[(3-bromo-1,4-dimethoxynaphthalen-2-yl)methylidene]-4-methoxybutanoate
• CAS: 1136840-08-8
• 化学式: C₁₉H₂₁BrO₅
• 分子量: 409.277
• InChiKey: FFPKQZGLYIYFGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-[(3-bromo-1,4-dimethoxynaphthalen-2-yl)methylidene]-4-methoxybutanoate 在 potassium hydroxide 、 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以35%的产率得到(E)-3-(3-bromo-1,4-dimethoxynaphthalen-2-yl)-2-methoxyethyl-2-propenoic acid
  参考文献：
  名称：

  Design and Synthesis of Novel Quinone Inhibitors Targeted to the Redox Function of Apurinic/Apyrimidinic Endonuclease 1/Redox Enhancing Factor-1 (Ape1/Ref-1)

  摘要：

  The multifunctional enzyme apurinic endonuclease 1/redox enhancing factor 1 (Apel/ref-1) maintains genetic fidelity through the repair of apurinic sites and regulates transcription through redox-dependent activation of transcription factors. Apel can therefore serve as a therapeutic target in either a DNA repair or transcriptional context. Inhibitors of the redox function can be used as either therapeutics or novel tools for separating the two functions for in vitro study. Presently there exist only a few compounds that have been reported to inhibit Apel redox activity; here we describe a series of quinones that exhibit micromolar inhibition of the redox function of Apel. Benzoquinone and naphthoquinone analogues of the Apel-inhibitor E3330 were designed and synthesized to explore structural effects on redox function and inhibition of cell growth. Most of the naphthoquinones were low micromolar inhibitors of Apel redox activity, and the most potent analogues inhibited tumor cell growth with IC50 values in the 10-20 mu M range.

  DOI：

  10.1021/jm9014857
• 作为产物：
  描述：

  3-[(3-bromo-1,4-dimethoxynaphthalen-2-yl)methylidene]oxolan-2-one 、 原甲酸三甲酯 在 硫酸 作用下， 以 甲醇 为溶剂， 以100%的产率得到Methyl 2-[(3-bromo-1,4-dimethoxynaphthalen-2-yl)methylidene]-4-methoxybutanoate
  参考文献：
  名称：

  Design and Synthesis of Novel Quinone Inhibitors Targeted to the Redox Function of Apurinic/Apyrimidinic Endonuclease 1/Redox Enhancing Factor-1 (Ape1/Ref-1)

  摘要：

  The multifunctional enzyme apurinic endonuclease 1/redox enhancing factor 1 (Apel/ref-1) maintains genetic fidelity through the repair of apurinic sites and regulates transcription through redox-dependent activation of transcription factors. Apel can therefore serve as a therapeutic target in either a DNA repair or transcriptional context. Inhibitors of the redox function can be used as either therapeutics or novel tools for separating the two functions for in vitro study. Presently there exist only a few compounds that have been reported to inhibit Apel redox activity; here we describe a series of quinones that exhibit micromolar inhibition of the redox function of Apel. Benzoquinone and naphthoquinone analogues of the Apel-inhibitor E3330 were designed and synthesized to explore structural effects on redox function and inhibition of cell growth. Most of the naphthoquinones were low micromolar inhibitors of Apel redox activity, and the most potent analogues inhibited tumor cell growth with IC50 values in the 10-20 mu M range.

  DOI：

  10.1021/jm9014857