3-((tert-butyldimethylsilyl)oxy)-4-methoxy-N-(3,4,5-trimethoxyphenyl)benzamide | 1355597-70-4

• 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: 3-((tert-butyldimethylsilyl)oxy)-4-methoxy-N-(3,4,5-trimethoxyphenyl)benzamide
• CAS: 1355597-70-4
• 化学式: C₂₃H₃₃NO₆Si
• 分子量: 447.604
• InChiKey: VLPYRUNEAHXBNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.25
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-((tert-butyldimethylsilyl)oxy)-4-methoxy-N-(3,4,5-trimethoxyphenyl)benzamide 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以98%的产率得到3-((tert-butyldimethylsilyl)oxy)-4-methoxy-N-(3,4,5-trimethoxyphenyl)benzothioamide
  参考文献：
  名称：

  A-Ring Dihalogenation Increases the Cellular Activity of Combretastatin-Templated Tetrazoles

  摘要：

  The combretastatins have been investigated for their antimitotic and antivascular properties, and it is widely postulated that a 3,4,5-trimethoxyaryl A-ring is essential to maintain potent activity. We have synthesized new tetrazole analogues (32-34), demonstrating that 3,5-dihalogenation can consistently increase potency by up to 5-fold when compared to the equivalent trimethoxy compound on human umbilical vein endothelial cells (HUVECs) and a range of cancer cells. Moreover, this increased potency offsets that lost by installing the tetrazole bridge into combretastatin A-4 (1), giving crystalline, soluble compounds that have low nanomolar activity, arrest cells in G(2)/M phase, and retain microtubule inhibitory activity. Molecular modeling has shown that optimized packing within the binding site resulting in increased Coulombic interaction may be responsible for this improved activity.

  DOI：

  10.1021/ml200149g
• 作为产物：
  描述：

  3-羟基-4-甲氧基苯甲酸 在 sodium hydride 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.0h， 生成 3-((tert-butyldimethylsilyl)oxy)-4-methoxy-N-(3,4,5-trimethoxyphenyl)benzamide
  参考文献：
  名称：

  A-Ring Dihalogenation Increases the Cellular Activity of Combretastatin-Templated Tetrazoles

  摘要：

  The combretastatins have been investigated for their antimitotic and antivascular properties, and it is widely postulated that a 3,4,5-trimethoxyaryl A-ring is essential to maintain potent activity. We have synthesized new tetrazole analogues (32-34), demonstrating that 3,5-dihalogenation can consistently increase potency by up to 5-fold when compared to the equivalent trimethoxy compound on human umbilical vein endothelial cells (HUVECs) and a range of cancer cells. Moreover, this increased potency offsets that lost by installing the tetrazole bridge into combretastatin A-4 (1), giving crystalline, soluble compounds that have low nanomolar activity, arrest cells in G(2)/M phase, and retain microtubule inhibitory activity. Molecular modeling has shown that optimized packing within the binding site resulting in increased Coulombic interaction may be responsible for this improved activity.

  DOI：

  10.1021/ml200149g