2-(2-methoxy-4-nitrophenylsulfonylamino)ethanol | 86919-14-4

• 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: 2-(2-methoxy-4-nitrophenylsulfonylamino)ethanol
• 英文别名: N-(2-hydroxyethyl)-2-methoxy-4-nitrobenzenesulfonamide
• CAS: 86919-14-4
• 化学式: C₉H₁₂N₂O₆S
• mdl: MFCD12073165
• 分子量: 276.27
• InChiKey: JZFWWJWMXRVVJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-methoxy-4-nitrophenylsulfonylamino)ethanol 在 sodium carbonate 、 三乙胺 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 8.5h， 生成 1-[2-(2-methoxy-4-nitrophenylsulfonylamino)ethyl]-4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Development of hypoxia-sensitive Gd3+-based MRI contrast agents

  摘要：

  Hypoxia occurs in various diseases, including cancer, ischemia, and acute and chronic vascular diseases. Here we describe the design and synthesis of the first hypoxia-sensitive MRI contrast agents, SAGds. SAGds showed a pH-dependent r(1) relaxivity change associated with intramolecular chelation of the nitrogen atom of the sulfonamide moiety to the Gd3+ center. There was a correlation between the pK(a) of the r(1) relaxivity change and the sum of the Hammett sigma constants of substituents on the aromatic ring. Among the synthesized compounds, 4NO(2)2MeOSAGd was selectively reduced to the amine by rat liver microsomes under hypoxic conditions, resulting in a 1.8-fold increment of the r(1) relaxivity owing to the change in pK(a) of the arylsulfonamide moiety. This enhancement of the r(1) relaxivity could be clearly detected in T-1-weighted MR images. Thus, 4NO(2)2MeOSAGd is a 'smart' MRI contrast agent for the detection of hypoxia under physiological conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.071
• 作为产物：
  描述：

  2-甲氧基-4-硝基苯磺酰氯 、 C.I.酸性橙108 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到2-(2-methoxy-4-nitrophenylsulfonylamino)ethanol
  参考文献：
  名称：

  Development of hypoxia-sensitive Gd3+-based MRI contrast agents

  摘要：

  Hypoxia occurs in various diseases, including cancer, ischemia, and acute and chronic vascular diseases. Here we describe the design and synthesis of the first hypoxia-sensitive MRI contrast agents, SAGds. SAGds showed a pH-dependent r(1) relaxivity change associated with intramolecular chelation of the nitrogen atom of the sulfonamide moiety to the Gd3+ center. There was a correlation between the pK(a) of the r(1) relaxivity change and the sum of the Hammett sigma constants of substituents on the aromatic ring. Among the synthesized compounds, 4NO(2)2MeOSAGd was selectively reduced to the amine by rat liver microsomes under hypoxic conditions, resulting in a 1.8-fold increment of the r(1) relaxivity owing to the change in pK(a) of the arylsulfonamide moiety. This enhancement of the r(1) relaxivity could be clearly detected in T-1-weighted MR images. Thus, 4NO(2)2MeOSAGd is a 'smart' MRI contrast agent for the detection of hypoxia under physiological conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.071

文献信息

• Development of hypoxia-sensitive Gd3+-based MRI contrast agents
  作者：Shimpei Iwaki、Kenjiro Hanaoka、Wen Piao、Toru Komatsu、Tasuku Ueno、Takuya Terai、Tetsuo Nagano

  DOI：10.1016/j.bmcl.2012.02.071

  日期：2012.4

  Hypoxia occurs in various diseases, including cancer, ischemia, and acute and chronic vascular diseases. Here we describe the design and synthesis of the first hypoxia-sensitive MRI contrast agents, SAGds. SAGds showed a pH-dependent r(1) relaxivity change associated with intramolecular chelation of the nitrogen atom of the sulfonamide moiety to the Gd3+ center. There was a correlation between the pK(a) of the r(1) relaxivity change and the sum of the Hammett sigma constants of substituents on the aromatic ring. Among the synthesized compounds, 4NO(2)2MeOSAGd was selectively reduced to the amine by rat liver microsomes under hypoxic conditions, resulting in a 1.8-fold increment of the r(1) relaxivity owing to the change in pK(a) of the arylsulfonamide moiety. This enhancement of the r(1) relaxivity could be clearly detected in T-1-weighted MR images. Thus, 4NO(2)2MeOSAGd is a 'smart' MRI contrast agent for the detection of hypoxia under physiological conditions. (C) 2012 Elsevier Ltd. All rights reserved.