(2,3-Dioxo-1,2,3,4-tetrahydro-quinoxalin-6-ylmethyl)-phosphonic acid | 459835-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (2,3-Dioxo-1,2,3,4-tetrahydro-quinoxalin-6-ylmethyl)-phosphonic acid
• 英文别名: Phosphonic acid, [(1,2,3,4-tetrahydro-2,3-dioxo-6-quinoxalinyl)methyl]-；(2,3-dioxo-1,4-dihydroquinoxalin-6-yl)methylphosphonic acid
• CAS: 459835-99-5
• 化学式: C₉H₉N₂O₅P
• 分子量: 256.155
• InChiKey: FFPODHBZFXBNOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氨基苄基磷酸二乙酯 在 吡啶 、 硝酸铵 、 titanium(III) chloride 、 三氟乙酸酐 作用下， 以 丙酮 为溶剂， 生成 (2,3-Dioxo-1,2,3,4-tetrahydro-quinoxalin-6-ylmethyl)-phosphonic acid
  参考文献：
  名称：

  5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition

  摘要：

  NMDA antagonists derived from 5-phosphonomethyl-1,4-dihydroquinoxaline-2,3-dione (3a) are potent anticonvulsant agents, and display strong protective effects in the electroshock-induced convulsion assay in mice. Their preference for the human NMDAR 1A/2A over 1A/2B subunit composition was optimized, leading to (1RS, 1'S)-PEAQX (9r), which shows a > 100-fold selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00074-4

文献信息

• [EN] A HIGH-THROUGHPUT ASSAY METHOD FOR IDENTIFYING ALLOSTERIC NMDA RECEPTOR MODULATORS<br/>[FR] MÉTHODE DE DOSAGE À HAUT DÉBIT POUR IDENTIFIER DES MODULATEURS DU RÉCEPTEUR DE NMDA ALLOSTÉRIQUES
  申请人：NOVARTIS AG

  公开号：WO2017109709A2

  公开（公告）日：2017-06-29

  A novel, high-throughput assay and methods to study N-methyl-D-aspartate receptors (NMDARs). The method allows for rapid comparisons of different subunits, the ability to measure effects of agonists for both the glycine binding site and the glutamate binding 5 site. The methods leverage the use of weak glycine and glutamate sites binding antagonists rather than to ketamine or MK-801 to mitigate against cellular toxicity and to retain the ligand binding site in a ligand-free state. The method can use baculovirus vectors to introduce titratable amounts of different receptor subunits. The assay replicates the pharmacology of NMDARs in response to known antagonists and allosteric 10 modulators, as well as sensitivity to magnesium.
• 5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition
  作者：Yves P Auberson、Hans Allgeier、Serge Bischoff、Kurt Lingenhoehl、Robert Moretti、Markus Schmutz

  DOI：10.1016/s0960-894x(02)00074-4

  日期：2002.4

  NMDA antagonists derived from 5-phosphonomethyl-1,4-dihydroquinoxaline-2,3-dione (3a) are potent anticonvulsant agents, and display strong protective effects in the electroshock-induced convulsion assay in mice. Their preference for the human NMDAR 1A/2A over 1A/2B subunit composition was optimized, leading to (1RS, 1'S)-PEAQX (9r), which shows a > 100-fold selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.