(2S)-2-amino-6-(2-nitro-5-methylphenylamino)hexanoic acid

• 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)-2-amino-6-(2-nitro-5-methylphenylamino)hexanoic acid
• 英文别名: (2S)-2-amino-6-(5-methyl-2-nitroanilino)hexanoic acid
• 化学式: C₁₃H₁₉N₃O₄
• 分子量: 281.312
• InChiKey: HFGRNJILQMQNQM-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-alpha-叔丁氧羰基-L-赖氨酸 在 盐酸 、 sodium hydroxide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 25.0h， 生成 (2S)-2-amino-6-(2-nitro-5-methylphenylamino)hexanoic 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

文献信息

• 2-nitroaryl and 2-cyanoaryl compounds as regulators of nitric oxide
  申请人：Abbott Laboratories

  公开号：US05362747A1

  公开（公告）日：1994-11-08

  2-Nitroaryl or 2-cyanoaryl compounds of the formula ##STR1## pharmaceutical compositions thereof, intermediates useful in the preparation of these compounds, and methods for treating disorders of vascular smooth muscles or diseases of the cartilage, macrophages, neurons, platelets, bronchial smooth muscles, optic muscles and gastrointestinal smooth muscles, in addition to sickle cell anemia, diabetes, synovitis, chondroarthritis and osteoarthritis by employing these compounds.

  本发明涉及式 ##STR1## 的2-硝基芳基或2-氰基芳基化合物、这些化合物的制备中间体、制药组合物以及使用这些化合物治疗血管平滑肌障碍或软骨、巨噬细胞、神经元、血小板、支气管平滑肌、视肌和胃肠平滑肌的疾病，以及镰状细胞贫血、糖尿病、滑膜炎、软骨关节炎和骨关节炎的方法。
• US5362747A
  申请人：——

  公开号：US5362747A

  公开（公告）日：1994-11-08
• [EN] 2-NITROARYL AND 2-CYANOARYL COMPOUNDS AS REGULATORS OF NITRIC OXIDE SYNTHASE<br/>[FR] COMPOSES 2-NITROARYLE ET 2-CYANOARYLE UTILISES COMME REGULATEURS DE SYNTHASE DE L'OXYDE NITRIQUE
  申请人：——

  公开号：WO1994012163A1

  公开（公告）日：1994-06-09

  [EN] 2-Nitroaryl or 2-cyanoaryl compounds of formula (I), pharmaceutical compositions thereof, intermediates useful in the preparation of these compounds, and methods for treating disorders of vascular smooth muscles or diseases of the cartilage, macrophages, neurons, platelets, bronchial smooth muscles, optic muscles and gastrointestinal smooth muscles, in addition to sickle cell anemia, diabetes, synovitis, chondroarthritis and osteoarthritis by employing these compounds.
  [FR] L'invention se rapporte à des composés 2-nitroaryle ou 2-cyanoaryle de la formule (I), à des compositions pharmaceutiques de ceux-ci, à des intermédiaires utiles dans la préparation de ces composés, et à des procédés visant à traiter les troubles des muscles lisses vasculaires ou les maladies du cartilage, des macrophages, des neurones, des thrombocytes, des muscles lisses bronchiques, des muscles optiques et des muscles lisses gastro-intestinaux, ainsi que la drépanocytose, les diabètes, les synovites, la chondroarthrite et l'ostéoarthrite par l'utilisation de ces composés.
• 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.