(S)-N-(4-nitrobenzoic)-glutamic acid | 1306671-36-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-(4-nitrobenzoic)-glutamic acid
• 英文别名: (S)-N-(4-nitrobenzoic)glutamic acid；N-p-nitrobenzoyl-L-glutamic acid；(2S)-2-[(4-nitrophenyl)methylamino]pentanedioic acid
• CAS: 1306671-36-2
• 化学式: C₁₂H₁₄N₂O₆
• 分子量: 282.253
• InChiKey: LWKQPMXDPPSLCI-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,4'-联吡啶 、 无水碳酸镉 、 (S)-N-(4-nitrobenzoic)-glutamic acid 、 水 以 水 为溶剂， 以21%的产率得到[[Cd((S)-N-(4-nitrobenzoic)-5-oxoproline(-1H))2(4,4'-bipyridine)]*2H2O](n)
  参考文献：
  名称：

  Homochiral coordination polymers constructed from aminocarboxylate derivates: Effect of bipyridine on the amidation reaction

  摘要：

  Using aminocarboxylate derivates (S)-N-(4-cyanobenzoic)-glutamic acid (denoted as cbg, la) and (S)-N-(4-nitrobenzoic)-glutamic acid (denoted as nbg, 1b) as chiral ligands, five new homochiral coordination polymers formulated as [Cu(cbg)(H2O)(2)](n) (3), [Cu(cbop)(2)(4,4'-bipy)(H2O)](n) (4) (cbop=(S)-N-(4-cyanobenzoic)-5-oxoproline, 4,4'-bipy=4,4'-bipyridine), {[Cu(nbop)(2)(4,4'-bipy)] center dot 4H(2)O}(n) (5) (nbop=(S)-N-(4-nitrobenzoic)-5-oxoproline), {[Cd(nbop)(2)(4,4'-bipy)] center dot 2H(2)O}(n) (6), and [Ni(nbop)(2)(4,4'-bipy)(H2O)(2)](n) (7) have been hydrothermally synthesized and structurally characterized. Single-crystal X-ray diffraction study reveals that the original chirality of aminocarboxylate derivates is maintained in all these complexes. Complexes 3, 4, and 7 are one-dimensional infinite chain coordination polymers, while complexes 5 and 6 possess two-dimensional network structures. In situ cyclization of 1a and 1b was taken place in the formation of complexes 4-7, which may be due to the competition of 4,4'-bipyridine with chiral ligands during the coordination process. Preliminary optical behavior investigation indicates that ligands 1a, 1b, and complexes 6, 7 are nonlinear optical active. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jssc.2012.04.025
• 作为产物：
  描述：

  L-谷氨酸 、 4-硝基苯甲酰氯 在 sodium acetate 、 sodium hydroxide 作用下， 反应 0.08h， 以64%的产率得到(S)-N-(4-nitrobenzoic)-glutamic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel nitroaromatic compounds as potent glutathione reductase inhibitors

  摘要：

  Discovery of GR inhibitors has become very popular recently due to antimalarial and anticancer activities. In this study, the synthesis and GR inhibitory capacities of novel nitroaromatic compounds (NCs) (1-3) were reported. Some commercially available molecules were also tested for comparison reasons. The novel NCs were obtained in high yields using simple chemical procedures and exhibited much potent inhibitory activities against GR at low micromolar concentrations with K-i values ranging from 0.211 to 4.57 mu M as compared with well-known agents. Inhibition mechanism was assessed as being due to occlusion of the active site entrance by means of the NCs. Molecular docking results have shown that docking poses of ligands are able to construct binding interactions with the essential amino acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.002

文献信息

• Design, synthesis and biological evaluation of novel nitroaromatic compounds as potent glutathione reductase inhibitors
  作者：Reşit Çakmak、Serdar Durdagi、Deniz Ekinci、Murat Şentürk、Giray Topal

  DOI：10.1016/j.bmcl.2011.07.002

  日期：2011.9

  Discovery of GR inhibitors has become very popular recently due to antimalarial and anticancer activities. In this study, the synthesis and GR inhibitory capacities of novel nitroaromatic compounds (NCs) (1-3) were reported. Some commercially available molecules were also tested for comparison reasons. The novel NCs were obtained in high yields using simple chemical procedures and exhibited much potent inhibitory activities against GR at low micromolar concentrations with K-i values ranging from 0.211 to 4.57 mu M as compared with well-known agents. Inhibition mechanism was assessed as being due to occlusion of the active site entrance by means of the NCs. Molecular docking results have shown that docking poses of ligands are able to construct binding interactions with the essential amino acids. (C) 2011 Elsevier Ltd. All rights reserved.
• Homochiral coordination polymers constructed from aminocarboxylate derivates: Effect of bipyridine on the amidation reaction
  作者：Jianshan Chen、Tianlu Sheng、Shengmin Hu、Shengchang Xiang、Ruibiao Fu、Qilong Zhu、Xintao Wu

  DOI：10.1016/j.jssc.2012.04.025

  日期：2012.8

  Using aminocarboxylate derivates (S)-N-(4-cyanobenzoic)-glutamic acid (denoted as cbg, la) and (S)-N-(4-nitrobenzoic)-glutamic acid (denoted as nbg, 1b) as chiral ligands, five new homochiral coordination polymers formulated as [Cu(cbg)(H2O)(2)](n) (3), [Cu(cbop)(2)(4,4'-bipy)(H2O)](n) (4) (cbop=(S)-N-(4-cyanobenzoic)-5-oxoproline, 4,4'-bipy=4,4'-bipyridine), [Cu(nbop)(2)(4,4'-bipy)] center dot 4H(2)O}(n) (5) (nbop=(S)-N-(4-nitrobenzoic)-5-oxoproline), [Cd(nbop)(2)(4,4'-bipy)] center dot 2H(2)O}(n) (6), and [Ni(nbop)(2)(4,4'-bipy)(H2O)(2)](n) (7) have been hydrothermally synthesized and structurally characterized. Single-crystal X-ray diffraction study reveals that the original chirality of aminocarboxylate derivates is maintained in all these complexes. Complexes 3, 4, and 7 are one-dimensional infinite chain coordination polymers, while complexes 5 and 6 possess two-dimensional network structures. In situ cyclization of 1a and 1b was taken place in the formation of complexes 4-7, which may be due to the competition of 4,4'-bipyridine with chiral ligands during the coordination process. Preliminary optical behavior investigation indicates that ligands 1a, 1b, and complexes 6, 7 are nonlinear optical active. (C) 2012 Elsevier Inc. All rights reserved.