2-chloro-3,4,5,6-tetramethoxybenzaldehyde | 1136839-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-3,4,5,6-tetramethoxybenzaldehyde
• CAS: 1136839-30-9
• 化学式: C₁₁H₁₃ClO₅
• 分子量: 260.674
• InChiKey: POGTWLQIWZDWFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  三乙基2-膦酰基丙酯 、 2-chloro-3,4,5,6-tetramethoxybenzaldehyde 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 ethyl (Z)-3-(2-chloro-3,4,5,6-tetramethoxyphenyl)-2-methyl-2-propenoate 、 ethyl (E)-3-(2-chloro-3,4,5,6-tetramethoxyphenyl)-2-methyl-2-propenoate
  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：

  2,3,4,5-tetramethoxybenzaldehyde 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以97%的产率得到2-chloro-3,4,5,6-tetramethoxybenzaldehyde
  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

文献信息

• Quinone derivatives, pharmaceutical compositions, and uses thereof
  申请人：Kelley Mark R.

  公开号：US09089605B2

  公开（公告）日：2015-07-28

  This application describes quinone derivatives which target the redox site of Ape1/Ref1. Also included in the invention are pharmaceutical formulations containing the derivatives and therapeutic uses of the derivatives.

  本申请描述了靶向Ape1/Ref1的氧化还原位点的醌衍生物。本发明还包括含有该衍生物的药物配方和该衍生物的治疗用途。
• QUINONE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF
  申请人：Kelley Mark R.

  公开号：US20100297113A1

  公开（公告）日：2010-11-25

  This application describes quinone derivatives which target the redox site of Ape1/Ref1. Also included in the invention are pharmaceutical formulations containing the derivatives and therapeutic uses of the derivatives.

  这个应用描述了目标为Ape1/Ref1的氧化还原位点的醌衍生物。发明还包括含有这些衍生物的药物制剂和这些衍生物的治疗用途。
• US9089605B2
  申请人：——

  公开号：US9089605B2

  公开（公告）日：2015-07-28
• [EN] QUINONE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF<br/>[FR] DÉRIVES DE QUINONE, COMPOSITIONS PHARMACEUTIQUES ET UTILISATIONS CORRESPONDANTES
  申请人：UNIV INDIANA RES & TECH CORP

  公开号：WO2009042544A1

  公开（公告）日：2009-04-02

  This application describes quinone derivatives which target the redox site of Ape1/Ref1. Also included in the invention are pharmaceutical formulations containing the derivatives and therapeutic uses of the derivatives.
• Design and Synthesis of Novel Quinone Inhibitors Targeted to the Redox Function of Apurinic/Apyrimidinic Endonuclease 1/Redox Enhancing Factor-1 (Ape1/Ref-1)
  作者：Rodney L. Nyland、Meihua Luo、Mark R. Kelley、Richard F. Borch

  DOI：10.1021/jm9014857

  日期：2010.2.11

  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.