2-amino-6-methylnicotinonitrile N-oxide | 1391062-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-6-methylnicotinonitrile N-oxide
• 英文别名: 2-amino-6-methylnicotinonitrile 1-oxide
• CAS: 1391062-94-4
• 化学式: C₇H₇N₃O
• 分子量: 149.152
• InChiKey: SWOXNMHOSSSHGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.75
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-amino-6-methylnicotinonitrile N-oxide 在 氨 作用下， 以 水 为溶剂， 80.0 ℃ 、827.39 kPa 条件下， 反应 0.25h， 以75%的产率得到2-amino-6-methylnicotinamide 1-oxide
  参考文献：
  名称：

  [EN] DERIVATIVES OF NICOTINIC ACID N-OXIDE, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF ENZYME 3-HYDROXYANTHRANILATE-3,4-DIOXYGENASE
  [FR] DÉRIVÉS DU N-OXYDE D'ACIDE NICOTINIQUE, LEUR PRÉPARATION ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE L'ENZYME 3-HYDROXYANTHRANILATE-3,4-DIOXYGÉNASE

  摘要：

  描述了一种烟酸N-氧化物的衍生物，其化学式为(I)：它作为酶3-羟基蒽醌-3,4-双氧酶（3HAO）的抑制剂，因此能够在兴奋毒性或病理条件下减少体内的喹啉（QUIN）生物合成，该化合物同时对自氧化具有化学稳定性。

  公开号：

  WO2012097869A1
• 作为产物：
  描述：

  2-氯-6-甲基-3-吡啶甲腈 在 氨 、 双氧水 、 甲基三氧化铼(VII) 作用下， 以 乙醇 、 水 为溶剂， 反应 80.0h， 生成 2-amino-6-methylnicotinonitrile N-oxide
  参考文献：
  名称：

  DERIVATIVES OF NICOTINIC ACID N-OXIDE, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF ENZYME 3-HYDROXYANTHRANILATE-3, 4-DIOXYGENASE

  摘要：

  描述了一种烟酸N-氧化物衍生物，其化学式为(I)，作为酶3-羟基蒽醌酸-3,4-双氧酶（3HAO）的抑制剂，因此能够在兴奋毒性或病理条件下减少体内的喹啉（QUIN）生物合成，该化合物同时也对自氧化具有化学稳定性。

  公开号：

  US20130289081A1

文献信息

• [EN] DERIVATIVES OF NICOTINIC ACID N-OXIDE, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF ENZYME 3-HYDROXYANTHRANILATE-3,4-DIOXYGENASE<br/>[FR] DÉRIVÉS DU N-OXYDE D'ACIDE NICOTINIQUE, LEUR PRÉPARATION ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE L'ENZYME 3-HYDROXYANTHRANILATE-3,4-DIOXYGÉNASE
  申请人：UNIV PARMA

  公开号：WO2012097869A1

  公开（公告）日：2012-07-26

  A derivative of nicotinic acid N-oxide is described having formula (I): that acts as inhibitor of enzyme 3-hydroxyanthranilate-3,4-dioxygenase (3HAO), and is thus able to reduce QUIN biosynthesis in vivo under excitotoxic or pathological conditions, said compound being at the same time also chemically stable towards auto-oxidation.

  描述了一种烟酸N-氧化物的衍生物，其化学式为(I)：它作为酶3-羟基蒽醌-3,4-双氧酶（3HAO）的抑制剂，因此能够在兴奋毒性或病理条件下减少体内的喹啉（QUIN）生物合成，该化合物同时对自氧化具有化学稳定性。
• DERIVATIVES OF NICOTINIC ACID N-OXIDE, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF ENZYME 3-HYDROXYANTHRANILATE-3, 4-DIOXYGENASE
  申请人：Schwarcz Robert

  公开号：US20130289081A1

  公开（公告）日：2013-10-31

  A derivative of nicotinic acid N-oxide is described having formula (I): that acts as inhibitor of enzyme 3-hydroxyanthranilate-3,4-dioxygenase (3HAO), and is thus able to reduce QUIN biosynthesis in vivo under excitotoxic or pathological conditions, said compound being at the same time also chemically stable towards auto-oxidation.

  描述了一种烟酸N-氧化物衍生物，其化学式为(I)，作为酶3-羟基蒽醌酸-3,4-双氧酶（3HAO）的抑制剂，因此能够在兴奋毒性或病理条件下减少体内的喹啉（QUIN）生物合成，该化合物同时也对自氧化具有化学稳定性。
• US9260394B2
  申请人：——

  公开号：US9260394B2

  公开（公告）日：2016-02-16
• US9487486B2
  申请人：——

  公开号：US9487486B2

  公开（公告）日：2016-11-08
• 2-Aminonicotinic Acid 1-Oxides Are Chemically Stable Inhibitors of Quinolinic Acid Synthesis in the Mammalian Brain: A Step toward New Antiexcitotoxic Agents
  作者：Gian Paolo Vallerini、Laura Amori、Claudia Beato、Margarita Tararina、Xiao-Dan Wang、Robert Schwarcz、Gabriele Costantino

  DOI：10.1021/jm401249c

  日期：2013.12.12

  3-Hydroxyanthranilic acid 3,4-dioxygenase (3-HAO) is the enzyme responsible for the production of the neurotoxic tryptophan metabolite quinolinic acid (QUIN). Elevated brain levels of QUIN are observed in several neurodegenerative diseases, but pharmacological investigation on its role in the pathogenesis of these conditions is difficult because only one class of substrate-analogue 3-HAO inhibitors, with poor chemical stability, has been reported so far. Here we describe the design, synthesis, and biological evaluation of a novel class of chemically stable inhibitors based on the 2-aminonicotinic acid 1-oxide nucleus. After the preliminary in vitro evaluation of newly synthesized compounds using brain tissue homogenate, we selected the most active inhibitor and showed its ability to acutely reduce the production of QUIN in the rat brain in vivo. These findings provide a novel pharmacological tool for the study of the mechanisms underlying the onset and propagation of neurodegenerative diseases.