4,5-dihydro-4-oxo[1,2,3]triazolo[1,5-a]quinoxaline-3-carboxylic acid | 113508-84-2

• 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: 4,5-dihydro-4-oxo[1,2,3]triazolo[1,5-a]quinoxaline-3-carboxylic acid
• 英文别名: 4-oxo-5H-triazolo[1,5-a]quinoxaline-3-carboxylic acid
• CAS: 113508-84-2
• 化学式: C₁₀H₆N₄O₃
• 分子量: 230.183
• InChiKey: QFZTYJJQDUKQCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-4-oxo[1,2,3]triazolo[1,5-a]quinoxaline-3-carboxylic acid 在 diphenyl ether-biphenyl eutectic 作用下， 反应 2.5h， 以80%的产率得到[1,2,3]三唑并[1,5-a]喹喔啉-4(5H)-酮
  参考文献：
  名称：

  1,2,3-Triazolo[1,5-a]quinoxalines: synthesis and binding to benzodiazepine and adenosine receptors

  摘要：

  This paper reports the synthesis and binding assays toward benzodiazepine and adenosine A(1) and A(2A) receptors of new 1,2,3-triazolo[1,5-a]quinoxalin-4-one derivatives. The prepared compounds show good affinity toward the benzodiazepine receptor (K-i 53-314 nM); the GABA ratio values suggest an inverse agonist activity for the N(5) unsubstituted compounds 6b-d and an agonist activity for the N(5) methylated compounds 7a-c. Some derivatives of both series show good affinity (Ki < 100 nM) and selectivity toward the adenosine A(1) receptorial subtype. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80036-6
• 作为产物：
  描述：

  1-叠氮基-2-硝基苯 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 31.0h， 生成 4,5-dihydro-4-oxo[1,2,3]triazolo[1,5-a]quinoxaline-3-carboxylic acid
  参考文献：
  名称：

  1,2,3-Triazolo[1,5-a]quinoxalines: synthesis and binding to benzodiazepine and adenosine receptors

  摘要：

  This paper reports the synthesis and binding assays toward benzodiazepine and adenosine A(1) and A(2A) receptors of new 1,2,3-triazolo[1,5-a]quinoxalin-4-one derivatives. The prepared compounds show good affinity toward the benzodiazepine receptor (K-i 53-314 nM); the GABA ratio values suggest an inverse agonist activity for the N(5) unsubstituted compounds 6b-d and an agonist activity for the N(5) methylated compounds 7a-c. Some derivatives of both series show good affinity (Ki < 100 nM) and selectivity toward the adenosine A(1) receptorial subtype. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80036-6

文献信息

• Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles
  作者：Ian R. Ager、Alan C. Barnes、Geoffrey W. Danswan、Peter W. Hairsine、David P. Kay、Peter D. Kennewell、Saroop S. Matharu、Peter Miller、Peter Robson

  DOI：10.1021/jm00401a009

  日期：1988.6

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.
• AGER, IAN R.;BARNES, ALAN C.;DANSWAN, GEOFFREY W.;HAIRSINE, PETER W.;KAY,+, J. MED. CHEM., 31,(1988) N 6, 1098-1115
  作者：AGER, IAN R.、BARNES, ALAN C.、DANSWAN, GEOFFREY W.、HAIRSINE, PETER W.、KAY,+

  DOI：——

  日期：——
• 1,2,3-Triazolo[1,5-a]quinoxalines: synthesis and binding to benzodiazepine and adenosine receptors
  作者：Lucia Bertelli、Giuliana Biagi、Irene Giorgi、Clementina Manera、Oreste Livi、Valerio Scartoni、Laura Betti、Gino Giannaccini、Letizia Trincavelli、Pier Luigi Barili

  DOI：10.1016/s0223-5234(98)80036-6

  日期：1998.2

  This paper reports the synthesis and binding assays toward benzodiazepine and adenosine A(1) and A(2A) receptors of new 1,2,3-triazolo[1,5-a]quinoxalin-4-one derivatives. The prepared compounds show good affinity toward the benzodiazepine receptor (K-i 53-314 nM); the GABA ratio values suggest an inverse agonist activity for the N(5) unsubstituted compounds 6b-d and an agonist activity for the N(5) methylated compounds 7a-c. Some derivatives of both series show good affinity (Ki < 100 nM) and selectivity toward the adenosine A(1) receptorial subtype. (C) Elsevier, Paris.