N-(2-hydroxyethyl)-2-(4-nitro-1H-imidazol-1-yl)acetamide | 1153126-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2-hydroxyethyl)-2-(4-nitro-1H-imidazol-1-yl)acetamide
• 英文别名: N-(2-hydroxyethyl)-2-(4-nitroimidazol-1-yl)acetamide
• CAS: 1153126-46-5
• 化学式: C₇H₁₀N₄O₄
• 分子量: 214.181
• InChiKey: JCLHJCMUTOCOCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-2-(4-nitro-1H-imidazol-1-yl)acetamide 、 bis-1,1‘-(4-sulfobutyl)indotricarbocyanine-5,5‘-dicarboxylic acid sodium salt 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以56%的产率得到
  参考文献：
  名称：

  Synthesis and fluorescent characteristics of imidazole–indocyanine green conjugates

  摘要：

  We have successfully synthesized imidazole-dye conjugates by linking imidazole and nitroimidazoleacetic acids to an indocyanine green (ICG) carboxylic acid derivative using an ethanolamine linker These dye-conjugates show absorbance peaks at 754-756 nm and fluorescence peaks at 780 rim The dye-conjugates show a blue shift of 25 nm and 30 nm in the absorption and fluorescence spectra respectively when compared to that of standard cardiogreen There is no change in absorption and fluorescence spectral profiles between the ICG derivative and imidazole conjugates The extinction coefficients of new ICG derivative and imidazole conjugates are 1 8 times higher than that of standard ICG The relative quantum yields of the new compounds are 4 5-5 5 times higher than that of the Sigma-Aldrich s ICG The dyes are tested for hypoxia in-vitro with 4T1 luc cell lines and it is found that the cells treated with 2-nitroimidazole ICG show a contrast of fluorescence signal of 2 5-30 for the cells under hypoxic to that of cells under normoxic However pure ICG shows no significant difference between hypoxic and normoxic cells (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.dyepig.2010.08.008
• 作为产物：
  描述：

  C.I.酸性橙108 、 (4-硝基咪唑-1-基)乙酸甲酯 以 甲醇 为溶剂， 反应 24.0h， 以0.587 g的产率得到N-(2-hydroxyethyl)-2-(4-nitro-1H-imidazol-1-yl)acetamide
  参考文献：
  名称：

  Synthesis and fluorescent characteristics of imidazole–indocyanine green conjugates

  摘要：

  We have successfully synthesized imidazole-dye conjugates by linking imidazole and nitroimidazoleacetic acids to an indocyanine green (ICG) carboxylic acid derivative using an ethanolamine linker These dye-conjugates show absorbance peaks at 754-756 nm and fluorescence peaks at 780 rim The dye-conjugates show a blue shift of 25 nm and 30 nm in the absorption and fluorescence spectra respectively when compared to that of standard cardiogreen There is no change in absorption and fluorescence spectral profiles between the ICG derivative and imidazole conjugates The extinction coefficients of new ICG derivative and imidazole conjugates are 1 8 times higher than that of standard ICG The relative quantum yields of the new compounds are 4 5-5 5 times higher than that of the Sigma-Aldrich s ICG The dyes are tested for hypoxia in-vitro with 4T1 luc cell lines and it is found that the cells treated with 2-nitroimidazole ICG show a contrast of fluorescence signal of 2 5-30 for the cells under hypoxic to that of cells under normoxic However pure ICG shows no significant difference between hypoxic and normoxic cells (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.dyepig.2010.08.008

文献信息

• Synthesis and fluorescent characteristics of imidazole–indocyanine green conjugates
  作者：Christopher Pavlik、Nrusingh C. Biswal、Faith Corbo Gaenzler、Martha D. Morton、Liisa T. Kuhn、Kevin P. Claffey、Quing Zhu、Michael B. Smith

  DOI：10.1016/j.dyepig.2010.08.008

  日期：2011.4

  We have successfully synthesized imidazole-dye conjugates by linking imidazole and nitroimidazoleacetic acids to an indocyanine green (ICG) carboxylic acid derivative using an ethanolamine linker These dye-conjugates show absorbance peaks at 754-756 nm and fluorescence peaks at 780 rim The dye-conjugates show a blue shift of 25 nm and 30 nm in the absorption and fluorescence spectra respectively when compared to that of standard cardiogreen There is no change in absorption and fluorescence spectral profiles between the ICG derivative and imidazole conjugates The extinction coefficients of new ICG derivative and imidazole conjugates are 1 8 times higher than that of standard ICG The relative quantum yields of the new compounds are 4 5-5 5 times higher than that of the Sigma-Aldrich s ICG The dyes are tested for hypoxia in-vitro with 4T1 luc cell lines and it is found that the cells treated with 2-nitroimidazole ICG show a contrast of fluorescence signal of 2 5-30 for the cells under hypoxic to that of cells under normoxic However pure ICG shows no significant difference between hypoxic and normoxic cells (C) 2010 Elsevier Ltd All rights reserved