ethyl (+/-)-6-chloro-1,2,3,4-tetrahydro-3-oxoquinoxaline-2-carboxylate | 350795-96-9

• 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: ethyl (+/-)-6-chloro-1,2,3,4-tetrahydro-3-oxoquinoxaline-2-carboxylate
• 英文别名: ethyl 6-chloro-3-oxo-2,4-dihydro-1H-quinoxaline-2-carboxylate
• CAS: 350795-96-9
• 化学式: C₁₁H₁₁ClN₂O₃
• 分子量: 254.673
• InChiKey: HMSWIIBZBRTSAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (+/-)-6-chloro-1,2,3,4-tetrahydro-3-oxoquinoxaline-2-carboxylate 在 盐酸 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 (7-Chloro-1,3,4-trioxo-3,3a,4,5-tetrahydro-imidazo[1,5-a]quinoxalin-2-yl)-acetic acid
  参考文献：
  名称：

  Synthesis of a set of ethyl 1-carbamoyl-3-oxoquinoxaline-2-carboxylates and of their constrained analogue imidazo[1,5-a]quinoxaline-1,3,4-triones as glycine/NMDA receptor antagonists

  摘要：

  The synthesis and glycine/NMDA and AMPA receptor affinities of a set of ethyl (+/-) 1-N-carbamoyl-1,2,3,4-tetrahydro-3-oxoquinoxaline-2-carboxylates 1-11 and those of their constrained analogue (+/-) 1,2,3,3a,4,5-hexahydroimidazo[1,5-a]quinoxaline 1,3,4-triones 12-24 are reported. Compounds 1-11 bear a side-chain at position 1 which has been spatially constrained in compounds 12-24. Most of the reported tricyclic derivatives 12-24 showed glycine/NMDA binding activity comparable to that of their corresponding bicyclic analogues 1-11 providing further evidence that the spatial orientation of the side-chain is an important structural requirement for glycine/NMDA receptor antagonists. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01203-4
• 作为产物：
  描述：

  6-氯-3-氧代-3,4-二氢喹噁啉-2-羧酸乙酯 在 sodium dithionite 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以50%的产率得到ethyl (+/-)-6-chloro-1,2,3,4-tetrahydro-3-oxoquinoxaline-2-carboxylate
  参考文献：
  名称：

  Synthesis of a set of ethyl 1-carbamoyl-3-oxoquinoxaline-2-carboxylates and of their constrained analogue imidazo[1,5-a]quinoxaline-1,3,4-triones as glycine/NMDA receptor antagonists

  摘要：

  The synthesis and glycine/NMDA and AMPA receptor affinities of a set of ethyl (+/-) 1-N-carbamoyl-1,2,3,4-tetrahydro-3-oxoquinoxaline-2-carboxylates 1-11 and those of their constrained analogue (+/-) 1,2,3,3a,4,5-hexahydroimidazo[1,5-a]quinoxaline 1,3,4-triones 12-24 are reported. Compounds 1-11 bear a side-chain at position 1 which has been spatially constrained in compounds 12-24. Most of the reported tricyclic derivatives 12-24 showed glycine/NMDA binding activity comparable to that of their corresponding bicyclic analogues 1-11 providing further evidence that the spatial orientation of the side-chain is an important structural requirement for glycine/NMDA receptor antagonists. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01203-4

文献信息

• [EN] 2-ACYLAMIDO DERIVATIVES OF 3,4-DIHYDRO-3-OXO-QUINOXALINE HAVING PHARMACEUTICAL ACTIVITY
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1992011245A1

  公开（公告）日：1992-07-09

  (EN) The present invention relates to novel 2-acylamide derivatives of 3,4-dihydro-3-oxo-quinoxaline useful as pharmaceutical agents, to methods for their production, to pharmaceutical compositions and methods of treatment therefor. The compounds of the present invention have activity as excitatory amino acid receptor mediators and, thus, are useful in the treatment of a wide range of neurodegenerative disorders including cerebrovascular disorders such as stroke.(FR) L'invention se rapporte à de nouveaux dérivés 2-acylamido de 3,4-dihydro-3-oxo-quinoxaline utilisés comme agents pharmaceutiques, à leurs procédés de production, à des compositions pharmaceutiques et à des procédés thérapeutiques les mettant en application. Les composés décrits par l'invention possèdent une activité de médiateurs de récepteurs d'acides aminés excitatoires et, de ce fait, ont une utilité thérapeutique dans le traitement d'un grand nombre de troubles neurodégénératifs, y compris les troubles cérébrovasculaires tels que les attaques.
• Synthesis of a set of ethyl 1-carbamoyl-3-oxoquinoxaline-2-carboxylates and of their constrained analogue imidazo[1,5-a]quinoxaline-1,3,4-triones as glycine/NMDA receptor antagonists
  作者：Flavia Varano、Daniela Catarzi、Vittoria Colotta、Lucia Cecchi、Guido Filacchioni、Alessandro Galli、Chiara Costagli

  DOI：10.1016/s0223-5234(00)01203-4

  日期：2001.2

  The synthesis and glycine/NMDA and AMPA receptor affinities of a set of ethyl (+/-) 1-N-carbamoyl-1,2,3,4-tetrahydro-3-oxoquinoxaline-2-carboxylates 1-11 and those of their constrained analogue (+/-) 1,2,3,3a,4,5-hexahydroimidazo[1,5-a]quinoxaline 1,3,4-triones 12-24 are reported. Compounds 1-11 bear a side-chain at position 1 which has been spatially constrained in compounds 12-24. Most of the reported tricyclic derivatives 12-24 showed glycine/NMDA binding activity comparable to that of their corresponding bicyclic analogues 1-11 providing further evidence that the spatial orientation of the side-chain is an important structural requirement for glycine/NMDA receptor antagonists. (C) 2001 Editions scientifiques et medicales Elsevier SAS.