2-[[4-[[4-(dimethylamino)phenyl]diazenyl]benzoyl]amino]acetic acid | 4238-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 2-[[4-[[4-(dimethylamino)phenyl]diazenyl]benzoyl]amino]acetic acid
• 英文别名: N-[4-[(1E)-2-[4-(dimethylamino)phenyl]diazenyl]benzoyl]-glycine；4-[(4-dimethylamino)phenylazo]benzoylglycine；N-[4-(4-dimethylamino-phenylazo)-benzoyl]-glycine；N-[4-(4-Dimethylamino-phenylazo)-benzoyl]-glycin
• CAS: 4238-39-5
• 化学式: C₁₇H₁₈N₄O₃
• 分子量: 326.355
• InChiKey: CJWMQZHWLJMCAQ-FMQUCBEESA-N

物化性质

• 熔点：
  238.0-240.0 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  612.5±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  94.36
• 氢给体数：
  2.0
• 氢受体数：
  5.0

安全信息

• 海关编码：
  2927000090

反应信息

• 作为反应物：
  描述：

  2-碘苯甲基溴 、 2-[[4-[[4-(dimethylamino)phenyl]diazenyl]benzoyl]amino]acetic acid 在 copper(l) iodide 、 四(三苯基膦)钯 、 caesium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 2-[3-[[(3',6'-dihydroxy-3-oxospiro[isobenzofuran-1(3H), 9'-[9H]xanthen]-6-yl)carbonyl]amino]-1-propyn-1-yl]-benzyl N-[4-[(1E)-2-[4-(dimethylamino)phenyl]diazenyl]benzoyl]-glycinate
  参考文献：
  名称：

  A specific molecular beacon probe for the detection of human prostate cancer cells

  摘要：

  The small-molecule, water-soluble molecular beacon probe 1 is hydrolyzed by the lysate and living cells of human prostate cancer cell lines (LNCaP), resulting in strong green fluorescence. In contrast, probe 1 does not undergo significant hydrolysis in either the lysate or living cells of human nontumorigenic prostate cells (RWPE-1). These results, corroborated by UV-Vis spectroscopy and fluorescent microscopy, reveal that probe 1 is a sensitive and specific fluorogenic and chromogenic sensor for the detection of human prostate cancer cells among nontumorigenic prostate cells and that carboxylesterase activity is a specific biomarker for human prostate cancer cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.055
• 作为产物：
  描述：

  ethyl N-[4-[(1E)-2-[4-(dimethylamino)phenyl] diazenyl]benzoyl]-glycinate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 以67%的产率得到2-[[4-[[4-(dimethylamino)phenyl]diazenyl]benzoyl]amino]acetic acid
  参考文献：
  名称：

  A specific molecular beacon probe for the detection of human prostate cancer cells

  摘要：

  The small-molecule, water-soluble molecular beacon probe 1 is hydrolyzed by the lysate and living cells of human prostate cancer cell lines (LNCaP), resulting in strong green fluorescence. In contrast, probe 1 does not undergo significant hydrolysis in either the lysate or living cells of human nontumorigenic prostate cells (RWPE-1). These results, corroborated by UV-Vis spectroscopy and fluorescent microscopy, reveal that probe 1 is a sensitive and specific fluorogenic and chromogenic sensor for the detection of human prostate cancer cells among nontumorigenic prostate cells and that carboxylesterase activity is a specific biomarker for human prostate cancer cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.055

文献信息

• DNA-Catalyzed Transfer of a Reporter Group
  作者：Tom N. Grossmann、Oliver Seitz

  DOI：10.1021/ja0670097

  日期：2006.12.1

  Herein we describe a novel DNA-catalyzed transfer of a reporter group from a donating to an accepting oligo-peptide nucleic acid (PNA), generating high catalytic turnover numbers in a DNA-sequence specific manner. The demonstrated transfer of the Dabcyl group was designed to switch on emission of a fluorescein dye while switching off emission of a rhodamine dye. This setup allows the highly sensitive and selective detection of DNA-sequences in real time.
• A specific molecular beacon probe for the detection of human prostate cancer cells
  作者：Yu Lin Jiang、Christopher A. McGoldrick、Deling Yin、Jing Zhao、Vini Patel、Marianne F. Brannon、Janet W. Lightner、Koyamangalath Krishnan、William L. Stone

  DOI：10.1016/j.bmcl.2012.04.055

  日期：2012.6

  The small-molecule, water-soluble molecular beacon probe 1 is hydrolyzed by the lysate and living cells of human prostate cancer cell lines (LNCaP), resulting in strong green fluorescence. In contrast, probe 1 does not undergo significant hydrolysis in either the lysate or living cells of human nontumorigenic prostate cells (RWPE-1). These results, corroborated by UV-Vis spectroscopy and fluorescent microscopy, reveal that probe 1 is a sensitive and specific fluorogenic and chromogenic sensor for the detection of human prostate cancer cells among nontumorigenic prostate cells and that carboxylesterase activity is a specific biomarker for human prostate cancer cells. (C) 2012 Elsevier Ltd. All rights reserved.