1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanedione dioxime | 852990-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanedione dioxime
• 英文别名: (NE)-N-[(2E)-1-[3-[tert-butyl(dimethyl)silyl]oxy-4-methoxyphenyl]-2-hydroxyimino-2-(3,4,5-trimethoxyphenyl)ethylidene]hydroxylamine
• CAS: 852990-36-4
• 化学式: C₂₄H₃₄N₂O₇Si
• 分子量: 490.629
• InChiKey: LXILLAOQJOLSRJ-CDTUYSNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanedione dioxime 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以93%的产率得到1-(3-hydroxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanedione dioxime
  参考文献：
  名称：

  Synthesis and Cytotoxic Evaluation of Combretafurazans

  摘要：

  Combretastatin A-4 is an antitumoral and antitubulin agent that is active only in its cis configuration. In the present manuscript, we have synthesized cis-locked combretastatins embodying a furazan ring (combretafurazans). To achieve this, we have developed a new strategy that exploits the dehydration of vicinal dioximes using the Mitsunobu reaction. Among the advantages of following such a strategy are the mild conditions used for the construction of the diarylfurazan derivatives, allowing for the presence of highly functionalized substrates and deactivated aromatic rings. Combretafurazans are more potent in vitro cytotoxic compounds compared to combretastatins in neuroblastoma cells, yet maintaining similar structure-activity relationship and pharmacodynamic profiles.

  DOI：

  10.1021/jm049096o
• 作为产物：
  描述：

  1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanedione 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以85%的产率得到1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanedione dioxime
  参考文献：
  名称：

  Synthesis and Cytotoxic Evaluation of Combretafurazans

  摘要：

  Combretastatin A-4 is an antitumoral and antitubulin agent that is active only in its cis configuration. In the present manuscript, we have synthesized cis-locked combretastatins embodying a furazan ring (combretafurazans). To achieve this, we have developed a new strategy that exploits the dehydration of vicinal dioximes using the Mitsunobu reaction. Among the advantages of following such a strategy are the mild conditions used for the construction of the diarylfurazan derivatives, allowing for the presence of highly functionalized substrates and deactivated aromatic rings. Combretafurazans are more potent in vitro cytotoxic compounds compared to combretastatins in neuroblastoma cells, yet maintaining similar structure-activity relationship and pharmacodynamic profiles.

  DOI：

  10.1021/jm049096o