6-methyl-7-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-5-carbonitrile | 573692-39-4

• 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: 6-methyl-7-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-5-carbonitrile
• CAS: 573692-39-4
• 化学式: C₁₀H₆N₄O₄
• 分子量: 246.182
• InChiKey: NDAANDCAYVWYPT-UHFFFAOYSA-N

物化性质

• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  132.65
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-methyl-7-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-5-carbonitrile 在 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以94%的产率得到7-amino-6-methyl-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-5-carbonitrile
  参考文献：
  名称：

  Synthesis and SAR of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones related to licostinel (Acea 1021) as NMDA/glycine site antagonists

  摘要：

  A series of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones (QXs) related to licostinel (Acea 1021) was synthesized and evaluated as antagonists for the glycine site of the N-methyl-D-asparate (NMDA) receptor. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [H-3]-5,7-dichlorokynurenic acid ([H-3]DCKA) in rat brain cortical membranes. Structure-activity relationship studies indicate that a cyano group is a good replacement for the nitro group in the 5-position of licostinel while 5-carboxy, 5-ester, 5-ketone and 5-amide derivatives showed reduced potency. 5,6-Cyclized analogues of licostinel also showed significantly reduced potency. Among the trisubstituted QXs investigated, 5-cyano-6,7-dichloro QX and 5-cyano-7-chloro-6-methyl QX are the most potent with IC50 values of 32 nM and 26 nM, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00059-2
• 作为产物：
  描述：

  2-chloro-6-methyl-3-nitrobenzonitrile 在 硝酸 、 三氟乙酸 、 tin(ll) chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 6-methyl-7-nitro-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-5-carbonitrile
  参考文献：
  名称：

  Synthesis and SAR of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones related to licostinel (Acea 1021) as NMDA/glycine site antagonists

  摘要：

  A series of novel di- and trisubstituted 1,4-dihydroquinoxaline-2,3-diones (QXs) related to licostinel (Acea 1021) was synthesized and evaluated as antagonists for the glycine site of the N-methyl-D-asparate (NMDA) receptor. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [H-3]-5,7-dichlorokynurenic acid ([H-3]DCKA) in rat brain cortical membranes. Structure-activity relationship studies indicate that a cyano group is a good replacement for the nitro group in the 5-position of licostinel while 5-carboxy, 5-ester, 5-ketone and 5-amide derivatives showed reduced potency. 5,6-Cyclized analogues of licostinel also showed significantly reduced potency. Among the trisubstituted QXs investigated, 5-cyano-6,7-dichloro QX and 5-cyano-7-chloro-6-methyl QX are the most potent with IC50 values of 32 nM and 26 nM, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00059-2