(1S,2R)-1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanediol | 852990-34-2

• 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: (1S,2R)-1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanediol
• 英文别名: (1S,2R)-1-[3-[tert-butyl(dimethyl)silyl]oxy-4-methoxyphenyl]-2-(3,4,5-trimethoxyphenyl)ethane-1,2-diol
• CAS: 852990-34-2
• 化学式: C₂₄H₃₆O₇Si
• 分子量: 464.631
• InChiKey: LWMRWPBWSYSVCW-FCHUYYIVSA-N

物化性质

• 沸点：
  548.1±50.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanediol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 四丁基氟化铵 、 potassium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 1-(3-Hydroxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane-1,2-dione
  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：

  (Z)-3,4,5,4',-四甲氧基-3'-羟基二苯乙烯 、 叔丁基二甲基氯硅烷 在 咪唑 、 AD-mix-α 、 甲基磺酰胺 、 叔丁醇 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 30.0h， 以29%的产率得到(1S,2R)-1-(3-{[tert-butyl(dimethyl)silyl]oxy}-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanediol
  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

文献信息

• Synthesis and Cytotoxic Evaluation of Combretafurazans
  作者：Gian Cesare Tron、Francesca Pagliai、Erika Del Grosso、Armando A. Genazzani、Giovanni Sorba

  DOI：10.1021/jm049096o

  日期：2005.5.1

  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.