<<3-(bromomethyl)benzoquinoxalin-2-yl>methyl>phosphonic acid dimethyl ester | 143154-22-7

• 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: <<3-(bromomethyl)benzoquinoxalin-2-yl>methyl>phosphonic acid dimethyl ester
• 英文别名: 3-(Bromomethyl)-2-(dimethoxyphosphorylmethyl)benzo[g]quinoxaline
• CAS: 143154-22-7
• 化学式: C₁₆H₁₆BrN₂O₃P
• 分子量: 395.192
• InChiKey: IFBRUXDTBMSCNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  <<3-(bromomethyl)benzoquinoxalin-2-yl>methyl>phosphonic acid dimethyl ester 在 三甲基溴硅烷 、 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 4.08h， 生成 α-amino-3-(phosphonomethyl)benzoquinoxaline-2-propanoic acid phenylmethyl ester
  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
• 作为产物：
  描述：

  2,3-二氨基萘 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲苯 、 苯 为溶剂， 反应 8.0h， 生成 <<3-(bromomethyl)benzoquinoxalin-2-yl>methyl>phosphonic acid dimethyl ester
  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