5-azido-1,3-dibromo-2-methoxybenzene | 1363602-98-5

• 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: 5-azido-1,3-dibromo-2-methoxybenzene
• 英文别名: 5-Azido-1,3-dibromo-2-methoxybenzene
• CAS: 1363602-98-5
• 化学式: C₇H₅Br₂N₃O
• 分子量: 306.944
• InChiKey: XVEFGJGYVWRYDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-azido-1,3-dibromo-2-methoxybenzene 、 tert-butyl(2-ethynyl-5-methoxyphenoxy)dimethylsilane 在 乙基氯化镁 、 氯化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 以64%的产率得到5-(2-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-1-(3,5-dibromo-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
• 作为产物：
  描述：

  4-氨基-2,6-二溴苯酚 在 盐酸 、 potassium carbonate 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 4.17h， 生成 5-azido-1,3-dibromo-2-methoxybenzene
  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

文献信息

• Increased endothelial cell selectivity of triazole-bridged dihalogenated A-ring analogues of combretastatin A–1
  作者：Thomas M. Beale、Peter J. Bond、James D. Brenton、D. Stephen Charnock-Jones、Steven V. Ley、Rebecca M. Myers

  DOI：10.1016/j.bmc.2012.01.010

  日期：2012.3

  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.