5-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-1-(3,5-dibromo-4-methoxyphenyl)-1H-tetrazole | 1355597-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-1-(3,5-dibromo-4-methoxyphenyl)-1H-tetrazole
• CAS: 1355597-84-0
• 化学式: C₂₁H₂₆Br₂N₄O₃Si
• 分子量: 570.356
• InChiKey: XFLCCLHVKCXLHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-1-(3,5-dibromo-4-methoxyphenyl)-1H-tetrazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以80%的产率得到5-(1-(3,5-dibromo-4-methoxyphenyl)-1H-tetrazol-5-yl)-2-methoxyphenol
  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：

  3,5-二溴-4-甲氧基苯胺 在 劳森试剂 、 叠氮基三甲基硅烷 、 mercury(II) diacetate 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 23.0h， 生成 5-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-1-(3,5-dibromo-4-methoxyphenyl)-1H-tetrazole
  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