methyl 3-(2-hydroxy-5-nitrophenyl)propanoate | 20921-10-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl 3-(2-hydroxy-5-nitrophenyl)propanoate
• 英文别名: β-(2-Hydroxy-5-nitro-phenyl)-propionsaeure-methylester
• CAS: 20921-10-2
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: OHZJBXOCBDDKLG-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  389.4±32.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  89.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-hydroxy-5-nitrophenyl)propanoate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium on activated charcoal 、 氢气 、 三乙胺 、 lithium chloride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.92h， 生成 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(2-(3-methoxy-3-oxopropyl)-4-(3-nitrobenzamido)phenyl)propanoate
  参考文献：
  名称：

  Design, synthesis and in vitro pharmacology of GluK1 and GluK3 antagonists. Studies towards the design of subtype-selective antagonists through 2-carboxyethyl-phenylalanines with substituents interacting with non-conserved residues in the GluK binding sites

  摘要：

  In order to identify compounds selective for the GluK1 and GluK3 subtypes of kainate receptors we have designed and synthesized a series of (S)-2-amino-3-((2-carboxyethyl)phenyl)propanoic acid analogs with hydrogen bond donating and accepting substituents on the aromatic ring. Based on crystal structures of GluK1 in complex with related ligands, the compounds were designed to explore possible interactions with non-conserved residues outside the glutamate ligand binding site and challenge the water binding network. Apart from obtaining GluK1 selective antagonists one analog with a phenyl-substituted urea (compound 31) showed some preference for GluK3 over GluK1-receptors. Docking studies indicate that this preference may be attributed to contacts between the NH of the urea substituent and non-conserved Ser741 and Ser761 residues.

  DOI：

  10.1016/j.bmc.2014.07.045
• 作为产物：
  描述：

  氢化肉桂酸内酯 在 硝酸 、 乙酸酐 作用下， 以 溶剂黄146 为溶剂， 反应 3.75h， 生成 methyl 3-(2-hydroxy-5-nitrophenyl)propanoate
  参考文献：
  名称：

  Design, synthesis and in vitro pharmacology of GluK1 and GluK3 antagonists. Studies towards the design of subtype-selective antagonists through 2-carboxyethyl-phenylalanines with substituents interacting with non-conserved residues in the GluK binding sites

  摘要：

  In order to identify compounds selective for the GluK1 and GluK3 subtypes of kainate receptors we have designed and synthesized a series of (S)-2-amino-3-((2-carboxyethyl)phenyl)propanoic acid analogs with hydrogen bond donating and accepting substituents on the aromatic ring. Based on crystal structures of GluK1 in complex with related ligands, the compounds were designed to explore possible interactions with non-conserved residues outside the glutamate ligand binding site and challenge the water binding network. Apart from obtaining GluK1 selective antagonists one analog with a phenyl-substituted urea (compound 31) showed some preference for GluK3 over GluK1-receptors. Docking studies indicate that this preference may be attributed to contacts between the NH of the urea substituent and non-conserved Ser741 and Ser761 residues.

  DOI：

  10.1016/j.bmc.2014.07.045

文献信息

• The photoinduced alcoholysis of 3,4-dihydrocoumarin and related compounds
  作者：C. David Gutsche、B. A. M. Oude-Alink

  DOI：10.1021/ja01023a034

  日期：1968.10