N-(2-hydroxyethyl)-2-(1H-imidazol-1-yl)acetamide | 1153125-92-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-hydroxyethyl)-2-(1H-imidazol-1-yl)acetamide
• 英文别名: N-(2-hydroxyethyl)-2-imidazol-1-ylacetamide
• CAS: 1153125-92-8
• 化学式: C₇H₁₁N₃O₂
• 分子量: 169.183
• InChiKey: NXYPTTCBTIYBGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  12
• 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：
  67.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-2-(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40%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 、 2-(1-咪唑基)乙酸甲酯 以 甲醇 为溶剂， 反应 24.0h， 以0.396 g的产率得到N-(2-hydroxyethyl)-2-(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 of β-hydroxyacetamides from unactivated ethyl acetates under base-free conditions and microwave irradiation
  作者：Eugenio Hernández-Fernández、Pedro Pablo Sánchez-Lara、Mario Ordóñez、Oscar Abelardo Ramírez-Marroquín、Francisco G. Avalos-Alanís、Susana López-Cortina、Víctor M. Jiménez-Pérez、Tannya Rocio Ibarra-Rivera

  DOI：10.1016/j.tetasy.2014.11.015

  日期：2015.1

  unactivated ethyl esters with achiral and chiral 1,2-amino alcohols under microwave irradiation and base-free conditions is described. This procedure provides a convenient method for the synthesis of β-hydroxyacetamides bearing pyrazole, imidazole, and benzimidazole groups in high yields and without racemization. The protocol described herein is environmentally friendly and allows for the preparation of a

  的酰胺化未活化乙酯与非手性和手性1,2-二氨基微波照射和游离碱条件下醇进行说明。该过程提供了β-hydroxyacetamides轴承吡唑，咪唑和苯并咪唑基团以高产率和无外消旋作用的合成的便利方法。本文所描述的协议是环境友好的，并且允许的各种β-hydroxyacetamides，这是在恶唑啉和生物学感兴趣的其它衍生物的合成中的关键中间体的制备。
• Detection of nucleic acid amplification
  申请人：Aivazachvili Vissarion

  公开号：US20070099211A1

  公开（公告）日：2007-05-03

  Methods for detecting a target polynucleotide sequences are provided that utilize a probe having a target-complementary segment and a detectable tag. By cleaving the detectable tab and associating the tag with a tag complement coupled to an electrode, an electrochemical signal can be detected that is related to the presence of the tag:tag complement complex.
• 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