(2S)-5-(5-methyl-2-nitroanilino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid | 159877-05-1

• 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: (2S)-5-(5-methyl-2-nitroanilino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
• CAS: 159877-05-1
• 化学式: C₁₇H₂₅N₃O₆
• 分子量: 367.402
• InChiKey: MJBPYSWBFHVXMQ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S)-5-(5-methyl-2-nitroanilino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid 在 盐酸 、 硼烷 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成
  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：

  3-氟-4-硝基甲苯 、 Boc-L-鸟氨酸 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (2S)-5-(5-methyl-2-nitroanilino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
  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