7-Bromo-5-(dimethoxyphosphorylmethyl)-2,3-dimethoxyquinoxaline | 187479-59-0

• 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: 7-Bromo-5-(dimethoxyphosphorylmethyl)-2,3-dimethoxyquinoxaline
• CAS: 187479-59-0
• 化学式: C₁₃H₁₆BrN₂O₅P
• 分子量: 391.158
• InChiKey: INHSPIVGQAJGIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-Bromo-5-(dimethoxyphosphorylmethyl)-2,3-dimethoxyquinoxaline 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 5-(Dimethoxyphosphorylmethyl)-2,3-dimethoxyquinoxaline
  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
• 作为产物：
  描述：

  7-bromo-5-bromomethyl-2,3-dimethoxy-quinoxaline 、 三甲氧基磷 以98%的产率得到7-Bromo-5-(dimethoxyphosphorylmethyl)-2,3-dimethoxyquinoxaline
  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

• NOVEL QUINOXALINE- AND QUINOXALINYLALKANE-PHOSPHONIC ACIDS
  申请人：Novartis AG

  公开号：EP0837864A1

  公开（公告）日：1998-04-29
• [EN] NOVEL QUINOXALINE- AND QUINOXALINYLALKANE-PHOSPHONIC ACIDS<br/>[FR] NOUVEAUX ACIDES QUINOXALINE- ET QUINOXALINYLALKANE-PHOSPHONIQUES
  申请人：NOVARTIS AG

  公开号：WO1997003079A1

  公开（公告）日：1997-01-30

  (EN) Quinoxaline- and quinoxalinylalkane-phosphonic acids of formula (I), wherein R1 is free or esterified carboxy or free or partially esterified phosphono, R2 and R3 are each independently of the other hydrogen or an aliphatic radical, the radicals R4, R5 and R6 are each independently of the others hydrogen, an aliphatic hydrocarbon radical, free or etherified hydroxy, free or etherified mercapto or oxidised free or etherified mercapto, unsubstituted or aliphatically substituted amino, nitro, free or esterified or amidated carboxy, cyano, free or amidated sulfamoyl, halogen or trifluoromethyl and X is a divalent aliphatic radical, and their tautomers and/or salts have NMDA-antagonistic properties and can be used in the treatment of pathological conditions that are responsive to blocking of NMDA-sensitive receptors.(FR) Cette invention concerne les acides quinoxaline- et quinoxalinylalkane-phosphoniques représentés par la formule (I), dans laquelle R1 est carboxy libre ou estérifié ou phosphono libre ou partiellement estérifié, R2 et R3 sont chacun, indépendamment l'un de l'autre, l'hydrogène ou un radical aliphatique, les radicaux R4, R5 et R6 sont chacun, indépendamment les uns des autres, l'hydrogène, un radical hydrocarbure aliphatique, hydroxy libre ou étherifié, mercapto libre ou étherifié ou mercapto oxydé libre ou étherifié, amino non substitué ou substitué par un radical aliphatique, nitro, carboxy libre ou estérifié ou amidé, cyano, sulfamoyle libre ou amidé, halogène ou trifluorométhyle et X est un radical aliphatique divalent. L'invention concerne également les tautomères de ces acides et/ou leurs sels qui sont dotés de propriétés antagonistes vis-à-vis de l'acide N-méthyl-D-aspartique (NMDA) et qui peuvent servir au traitement d'états pathologiques qui répondent à un blocage des récepteurs sensibles au NMDA.
• 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.