ethyl 2-hydroxy-3-nitrobenzenepropanoate | 54892-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: ethyl 2-hydroxy-3-nitrobenzenepropanoate
• 英文别名: 3-(3-Nitro-2-hydroxy-phenyl)-propionsaeure-aethylester；Ethyl 3-(2-hydroxy-3-nitrophenyl)propanoate
• CAS: 54892-94-3
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: IRRVFPSTZRQTIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-hydroxy-3-nitrobenzenepropanoate 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙酸乙酯 为溶剂， 25.0~65.0 ℃ 、206.84 kPa 条件下， 反应 1.5h， 生成 ethyl 2-<(6-phenylhexyl)oxy>-3-aminobenzenepropanoate
  参考文献：
  名称：

  Benzophenone dicarboxylic acid antagonists of leukotriene B4. 1. Structure-activity relationships of the benzophenone nucleus

  摘要：

  A series of lipophilic benzophenone dicarboxylic acid derivatives was prepared which inhibited the binding of the potent chemotaxin leukotriene B4 to its receptor(s) on intact human neutrophils. With a radioligand-binding assay as a measure of receptor affinity, a structure-activity relationship for this series was investigated. Both acidic residues were required for receptor-binding activity. The relative orientation of the two acidic groups was important for optimal binding. Replacement of the carbonyl group of the benzophenone with a variety of polar and nonpolar linking groups led to only small changes in binding affinity, indicating the linking group may not be involved in receptor recognition. Further structure-activity relationships within this series are reported in an accompanying paper.

  DOI：

  10.1021/jm00172a019
• 作为产物：
  描述：

  2-羟基-苯丙酸乙酯 在 硝酸 、 溶剂黄146 作用下， 反应 0.5h， 以28%的产率得到ethyl 2-hydroxy-3-nitrobenzenepropanoate
  参考文献：
  名称：

  Benzophenone dicarboxylic acid antagonists of leukotriene B4. 1. Structure-activity relationships of the benzophenone nucleus

  摘要：

  A series of lipophilic benzophenone dicarboxylic acid derivatives was prepared which inhibited the binding of the potent chemotaxin leukotriene B4 to its receptor(s) on intact human neutrophils. With a radioligand-binding assay as a measure of receptor affinity, a structure-activity relationship for this series was investigated. Both acidic residues were required for receptor-binding activity. The relative orientation of the two acidic groups was important for optimal binding. Replacement of the carbonyl group of the benzophenone with a variety of polar and nonpolar linking groups led to only small changes in binding affinity, indicating the linking group may not be involved in receptor recognition. Further structure-activity relationships within this series are reported in an accompanying paper.

  DOI：

  10.1021/jm00172a019

文献信息

• GAPINSKI, D. MARK;MALLETT, BARBARA E.;FROELICH, LARRY L.;JACKSON, WILLIAM+, J. MED. CHEM., 33,(1990) N0, C. 2798-2807
  作者：GAPINSKI, D. MARK、MALLETT, BARBARA E.、FROELICH, LARRY L.、JACKSON, WILLIAM+

  DOI：——

  日期：——
• US4992576A
  申请人：——

  公开号：US4992576A

  公开（公告）日：1991-02-12
• US5171882A
  申请人：——

  公开号：US5171882A

  公开（公告）日：1992-12-15
• US5235064A
  申请人：——

  公开号：US5235064A

  公开（公告）日：1993-08-10
• Benzophenone dicarboxylic acid antagonists of leukotriene B4. 1. Structure-activity relationships of the benzophenone nucleus
  作者：D. Mark Gapinski、Barbara E. Mallett、Larry L. Froelich、William T. Jackson

  DOI：10.1021/jm00172a019

  日期：1990.10

  A series of lipophilic benzophenone dicarboxylic acid derivatives was prepared which inhibited the binding of the potent chemotaxin leukotriene B4 to its receptor(s) on intact human neutrophils. With a radioligand-binding assay as a measure of receptor affinity, a structure-activity relationship for this series was investigated. Both acidic residues were required for receptor-binding activity. The relative orientation of the two acidic groups was important for optimal binding. Replacement of the carbonyl group of the benzophenone with a variety of polar and nonpolar linking groups led to only small changes in binding affinity, indicating the linking group may not be involved in receptor recognition. Further structure-activity relationships within this series are reported in an accompanying paper.