2,3-Bis(bromomethyl)-6,7-dimethoxyquinoxaline | 33561-34-1

• 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-Bis(bromomethyl)-6,7-dimethoxyquinoxaline
• 英文别名: Quinoxaline, 2,3-bis(bromomethyl)-6,7-dimethoxy-
• CAS: 33561-34-1
• 化学式: C₁₂H₁₂Br₂N₂O₂
• 分子量: 376.047
• InChiKey: CUUNBRSTYACOSY-UHFFFAOYSA-N

物化性质

• 沸点：
  405.3±40.0 °C(Predicted)
• 密度：
  1.733±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-Bis(bromomethyl)-6,7-dimethoxyquinoxaline 在 哌啶 作用下， 以 甲醇 为溶剂， 反应 18.5h， 生成 1,4-Dimethoxy-7,8-dimethyl-6,9-dipyridiniophenazine dibromide
  参考文献：
  名称：

  Synthesis of some substituted quinoxalines and polycyclic systems containing the quinoxaline nucleus

  摘要：

  所述的合成包括作为中间体的喹唑啉11、14、15、16、20、21、23和25。讨论了从3通过硫脲作用制备21以及从硫化物20和正丁胺形成六氮五元环23的过程。重新研究了二酮10的甲基化，发现产物为29和30的混合物。描述了二甲氧基喹唑啉穴合配体（如32、33、34、40和41）、三环冠醚31和五环冠醚（如38）的制备，并报道了金属离子对40和41光谱性质的影响。

  DOI：

  10.1039/p19960002443
• 作为产物：
  描述：

  1,2-二甲氧基-4-二硝基苯 在 palladium on activated charcoal 氢气 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 2,3-Bis(bromomethyl)-6,7-dimethoxyquinoxaline
  参考文献：
  名称：

  Potent quinoxaline-spaced phosphono .alpha.-amino acids of the AP-6 type as competitive NMDA antagonists: synthesis and biological evaluation

  摘要：

  A series of alpha-amino-3-(phosphonoalkyl)-2-quinoxalinepropanoic acids was synthesized and evaluated for NMDA receptor affinity using a[H-3]CPP binding assay. Functional antagonism of the NMDA receptor complex was evaluated in vitro using a stimulated [H-3]TCP binding assay and in vivo by employing an NMDA-induced seizure model. Some analogues also were evaluated in the [H-3]-glycine binding assay. Several compounds of the AP-6 type show potent and selective NMDA antagonistic activity both in vitro and in vivo. In particular alpha-amino-7-chloro-3-(phosphonomethyl)-2-quinoxalinepropanoic acid (1) displayed an ED50 Of 1.1 mg/kg ip in the NMDA lethality model. Noteworthy is alpha-amino-6,7-dichloro-3-(phosphonomethyl)-2-quinoxalinepropanoic acid (3) with a unique dual activity, displaying in the NMDA receptor binding assay an IC50 of 3.4 nM and in the glycine binding assay an IC50 of 0.61 muM.

  DOI：

  10.1021/jm00055a004

文献信息

• US5118675A
  申请人：——

  公开号：US5118675A

  公开（公告）日：1992-06-02
• [EN] QUINOXALINE PHOSPHONO-AMINO ACIDS
  申请人：——

  公开号：WO1992014740A1

  公开（公告）日：1992-09-03

  [FR] On décrit des composés de la formule (I) où Q représente le noyau de quinoxaline; m représente l'un des nombres entiers 0, 1 ou 2; n représente l'un des nombres entiers 1, 2 ou 3; ou un sel pharmaceutiquement acceptable, un ester d'alkyle ou (II) où R3 et R4 représentent indépendamment hydrogène, nitro, halo ou méthoxy. Ces composés sont des antagonistes de N-méthyle-D-Aspartate pouvant être utilisés pour le traitement et la prévention d'états pathologiques associés au système nerveux central et produits par une stimulation excessive des aminoacides excitateurs.
  [EN] The compounds of formula (I), in which Q is the quinoxaline nucleus; m is one of the integers 0, 1 or 2; n is one of the integers 1, 2 or 3; or a pharmaceutically acceptable salt, alkyl ester or (II) where R?3 and R?4 are, independently, hydrogen, nitro, halo or methoxy, are NMDA antagonists useful in the treatment and prevention of central nervous system related pathological conditions resulting from overstimulation by excitatory amino acids.
• Synthesis of some substituted quinoxalines and polycyclic systems containing the quinoxaline nucleus
  作者：Abid R. Ahmad、Lina K. Mehta、John Parrick

  DOI：10.1039/p19960002443

  日期：——

  The synthesis is described of quinoxalines 11, 14, 15, 16, 20, 21, 23 and 25 of interest as intermediates. The preparation of 21 from 3 by the action of thiourea and the formation of the hexaazapentacycle 23 from sulfide 20 and butylamine are discussed. The methylation of the dione 10 is reinvestigated and the product found to be a mixture of 29 and 30. The preparation of dimethoxyquinoxaline podands, e.g., 32, 33, 34, 40 and 41, tricyclic crown ether 31 and pentacyclic crown ethers, e.g. 38, is described and the effects of metal ions on spectroscopic properties of 40 and 41 are reported.

  所述的合成包括作为中间体的喹唑啉11、14、15、16、20、21、23和25。讨论了从3通过硫脲作用制备21以及从硫化物20和正丁胺形成六氮五元环23的过程。重新研究了二酮10的甲基化，发现产物为29和30的混合物。描述了二甲氧基喹唑啉穴合配体（如32、33、34、40和41）、三环冠醚31和五环冠醚（如38）的制备，并报道了金属离子对40和41光谱性质的影响。
• Potent quinoxaline-spaced phosphono .alpha.-amino acids of the AP-6 type as competitive NMDA antagonists: synthesis and biological evaluation
  作者：Reinhardt B. Baudy、Lynne P. Greenblatt、Ivo L. Jirkovsky、Mary Conklin、Ralph J. Russo、Donna R. Bramlett、Tracy A. Emrey、Joanne T. Simmonds、Dianne M. Kowal

  DOI：10.1021/jm00055a004

  日期：1993.2

  A series of alpha-amino-3-(phosphonoalkyl)-2-quinoxalinepropanoic acids was synthesized and evaluated for NMDA receptor affinity using a[H-3]CPP binding assay. Functional antagonism of the NMDA receptor complex was evaluated in vitro using a stimulated [H-3]TCP binding assay and in vivo by employing an NMDA-induced seizure model. Some analogues also were evaluated in the [H-3]-glycine binding assay. Several compounds of the AP-6 type show potent and selective NMDA antagonistic activity both in vitro and in vivo. In particular alpha-amino-7-chloro-3-(phosphonomethyl)-2-quinoxalinepropanoic acid (1) displayed an ED50 Of 1.1 mg/kg ip in the NMDA lethality model. Noteworthy is alpha-amino-6,7-dichloro-3-(phosphonomethyl)-2-quinoxalinepropanoic acid (3) with a unique dual activity, displaying in the NMDA receptor binding assay an IC50 of 3.4 nM and in the glycine binding assay an IC50 of 0.61 muM.