2-(1-(3,5-dibromo-4-methoxyphenyl)-1H-1,2,3-triazol-5-yl)-5-methoxyphenol | 1363603-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(1-(3,5-dibromo-4-methoxyphenyl)-1H-1,2,3-triazol-5-yl)-5-methoxyphenol
• 英文别名: 2-[3-(3,5-Dibromo-4-methoxyphenyl)triazol-4-yl]-5-methoxyphenol；2-[3-(3,5-dibromo-4-methoxyphenyl)triazol-4-yl]-5-methoxyphenol
• CAS: 1363603-26-2
• 化学式: C₁₆H₁₃Br₂N₃O₃
• 分子量: 455.106
• InChiKey: QLQGNEVWHFSINZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氨基-2,6-二溴苯酚 在 盐酸 、 四丁基氟化铵 、 乙基氯化镁 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 8.67h， 生成 2-(1-(3,5-dibromo-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