N-叔丁氧羰基-N’-(2,4-二硝基苯基)-L-鸟氨酸 | 82518-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-叔丁氧羰基-N’-(2,4-二硝基苯基)-L-鸟氨酸
• 中文别名: (S)-2-((叔丁氧基羰基)氨基)-5-((2,4-二硝基苯基)氨基)戊酸；N-叔丁氧羰基-N'-(2,4-二硝基苯基)-L-鸟氨酸
• 英文名称: N^δ-DNP-N^α-t-butoxycarbonyl-L-ornithine
• 英文别名: (S)-2-((tert-Butoxycarbonyl)amino)-5-((2,4-dinitrophenyl)amino)pentanoic acid；(2S)-5-(2,4-dinitroanilino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
• CAS: 82518-61-4
• 化学式: C₁₆H₂₂N₄O₈
• 分子量: 398.373
• InChiKey: PXVAXTMGYWSFHF-LBPRGKRZSA-N

物化性质

• 沸点：
  639.3±55.0 °C(Predicted)
• 密度：
  1.380

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  179
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-N’-(2,4-二硝基苯基)-L-鸟氨酸 在 盐酸 、 溶剂黄146 作用下， 反应 1.0h， 生成 N^δ-(2.4-dinitro-phenyl)-L-ornithine ; hydrochloride
  参考文献：
  名称：

  Nitroaromatic Amino Acids as Inhibitors of Neuronal Nitric Oxide Synthase

  摘要：

  Nitric oxide (NO .) is an important biomodulator of many physiological processes. The inhibition of inappropriate production of NO . by the isoforms of nitric oxide synthase (NOS) has been proposed as a therapeutic approach for the treatment of stroke, inflammation, and other processes. In this study, certain 2-nitroaryl-substituted amino acid analogues were discovered to inhibit NOS. Analogues bearing a 5-methyl substituent on the aromatic ring demonstrated maximal inhibitory potency. For two selected inhibitors, investigation of the kinetics of the enzyme showed the inhibition to be competitive with L-arginine. Additionally, functional NOS inhibition in tissue preparations was demonstrated.

  DOI：

  10.1021/jm980073h
• 作为产物：
  描述：

  2,4-二硝基氟苯 、 Boc-L-鸟氨酸 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 N-叔丁氧羰基-N’-(2,4-二硝基苯基)-L-鸟氨酸
  参考文献：
  名称：

  Nitroaromatic Amino Acids as Inhibitors of Neuronal Nitric Oxide Synthase

  摘要：

  Nitric oxide (NO .) is an important biomodulator of many physiological processes. The inhibition of inappropriate production of NO . by the isoforms of nitric oxide synthase (NOS) has been proposed as a therapeutic approach for the treatment of stroke, inflammation, and other processes. In this study, certain 2-nitroaryl-substituted amino acid analogues were discovered to inhibit NOS. Analogues bearing a 5-methyl substituent on the aromatic ring demonstrated maximal inhibitory potency. For two selected inhibitors, investigation of the kinetics of the enzyme showed the inhibition to be competitive with L-arginine. Additionally, functional NOS inhibition in tissue preparations was demonstrated.

  DOI：

  10.1021/jm980073h

文献信息

• Upon DNP-aromatic Rule. Effect of Chromophore Exchange on the CD Spectra of<i>N</i>-DNP-arylalkylamines
  作者：Masao Kawai、Ukon Nagai

  DOI：10.1246/bcsj.55.1327

  日期：1982.4

  CD spectra of the analogs of aromatic DNP-α-amino acids and the related N-DNP-arylalkylamines, in which the positions of the two chromophoric groups were exchanged with each other, were studied. The analogs, in which the DNP-amino group is separated from the asymmetric carbon, did not show any marked Cotton effect near 400 nm, indicating the importance of direct attachment of the DNP–NH group to the chiral carbon atom for showing the characteristic CD spectra of N-DNP-aromatic α-amino acids.

  对芳香族DNP-α-氨基酸类似物和相关的N-DNP-芳基烷基胺（其中两个发色团的位置相互交换）的CD光谱进行了研究。在DNP-氨基与不对称碳原子分离的类似物中，在400 nm附近没有出现明显的棉花效应，这表明DNP-NH基团直接连接到手性碳原子对于显示N-DNP-芳香族α-氨基酸的特征CD光谱非常重要。
• Nitroaromatic Amino Acids as Inhibitors of Neuronal Nitric Oxide Synthase
  作者：Marlon Cowart、Elizabeth A. Kowaluk、Jerome F. Daanen、Kathy L. Kohlhaas、Karen M. Alexander、Frank L. Wagenaar、James F. Kerwin

  DOI：10.1021/jm980073h

  日期：1998.7.1

  Nitric oxide (NO .) is an important biomodulator of many physiological processes. The inhibition of inappropriate production of NO . by the isoforms of nitric oxide synthase (NOS) has been proposed as a therapeutic approach for the treatment of stroke, inflammation, and other processes. In this study, certain 2-nitroaryl-substituted amino acid analogues were discovered to inhibit NOS. Analogues bearing a 5-methyl substituent on the aromatic ring demonstrated maximal inhibitory potency. For two selected inhibitors, investigation of the kinetics of the enzyme showed the inhibition to be competitive with L-arginine. Additionally, functional NOS inhibition in tissue preparations was demonstrated.