2-(4-methoxy-2-nitrophenylsulfonylamino)ethanol | 1050514-15-2

• 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-(4-methoxy-2-nitrophenylsulfonylamino)ethanol
• 英文别名: N-(2-hydroxyethyl)-4-methoxy-2-nitrobenzenesulfonamide
• CAS: 1050514-15-2
• 化学式: C₉H₁₂N₂O₆S
• mdl: MFCD12073192
• 分子量: 276.27
• InChiKey: AAVXHOHSTGQICU-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-(4-methoxy-2-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 5.5h， 生成
  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：

  4-甲氧基-2-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93%的产率得到2-(4-methoxy-2-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

• Quinoxaline Compounds and Use Thereof
  申请人：Gaillard Pascale

  公开号：US20100137308A1

  公开（公告）日：2010-06-03

  The present invention is related to quinoxaline compounds of Formula (I) in particular for the treatment of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.

  本发明涉及一种公式（I）的喹啉化合物，特别用于治疗自身免疫性疾病和/或炎症性疾病、心血管疾病、神经退行性疾病、细菌或病毒感染、肾脏疾病、血小板聚集、癌症、移植、移植排斥或肺损伤。
• Quinoxaline inhibitors of phosphoinositide-3-kinases (PI3Ks)
  申请人：Gaillard Pascale

  公开号：US08614215B2

  公开（公告）日：2013-12-24

  The present invention is related to quinoxaline compounds of Formula (I) in particular for the treatment of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.

  本发明涉及式（I）的喹喔啉化合物，特别是用于治疗自身免疫性疾病和/或炎症性疾病、心血管疾病、神经退行性疾病、细菌或病毒感染、肾脏疾病、血小板聚集、癌症、移植、移植排斥或肺损伤。
• WO2008/101979
  申请人：——

  公开号：——

  公开（公告）日：——
• QUINOXALINE COMPOUNDS AND USE THEREOF
  申请人：Merck Serono S.A.

  公开号：EP2118076A1

  公开（公告）日：2009-11-18
• US8614215B2
  申请人：——

  公开号：US8614215B2

  公开（公告）日：2013-12-24