5-(2-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-1-(3,5-diiodo-4-methoxyphenyl)-1H-1,2,3-triazole | 1380079-63-9

• 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-(2-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-1-(3,5-diiodo-4-methoxyphenyl)-1H-1,2,3-triazole
• CAS: 1380079-63-9
• 化学式: C₂₂H₂₇I₂N₃O₃Si
• 分子量: 663.369
• InChiKey: MOTCGHUCAATDST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 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：
  0.36
• 拓扑面积：
  58.4
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-(2-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-1-(3,5-diiodo-4-methoxyphenyl)-1H-1,2,3-triazole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到2-(1-(3,5-diiodo-4-methoxyphenyl)-1H-1,2,3-triazol-5-yl)-5-methoxyphenol
  参考文献：
  名称：

  Increased endothelial cell selectivity of triazole-bridged dihalogenated A-ring analogues of combretastatin A–1

  摘要：

  The antiproliferative activity on ovarian cancer (SK-OV-3) cells of a series of triazole-bridged combretastatin analogues (37, 38, 40-43) containing dihalogenation of the A-ring is reported, and compared with their trimethoxy analogues (5, 15, 39). It was found that dihalogenation with either bromine or iodine was a tolerated modification when compared to the parent compound combretastatin (CA-4, 1) and had less effect than B-ring modification on potency. These compounds exhibited G(2)/M arrest, and maintained antitubulin activity. Further assays on human umbilical vein endothelial cells (HUVECs) demonstrated the potential antivascular effects of these triazoles. Of particular note was a 3,5-diiodo-4-methoxyaryl triazole (43) which had promising 7-fold selectivity for HUVECs over ovarian cancer cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.010
• 作为产物：
  描述：

  2,6-二碘-4-硝基苯酚 在 盐酸 、 乙醇 、 乙基氯化镁 、 potassium carbonate 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 26.5h， 生成 5-(2-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-1-(3,5-diiodo-4-methoxyphenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Increased endothelial cell selectivity of triazole-bridged dihalogenated A-ring analogues of combretastatin A–1

  摘要：

  The antiproliferative activity on ovarian cancer (SK-OV-3) cells of a series of triazole-bridged combretastatin analogues (37, 38, 40-43) containing dihalogenation of the A-ring is reported, and compared with their trimethoxy analogues (5, 15, 39). It was found that dihalogenation with either bromine or iodine was a tolerated modification when compared to the parent compound combretastatin (CA-4, 1) and had less effect than B-ring modification on potency. These compounds exhibited G(2)/M arrest, and maintained antitubulin activity. Further assays on human umbilical vein endothelial cells (HUVECs) demonstrated the potential antivascular effects of these triazoles. Of particular note was a 3,5-diiodo-4-methoxyaryl triazole (43) which had promising 7-fold selectivity for HUVECs over ovarian cancer cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.010