(3-Chloro-7-fluoro-quinoxalin-2-yl)-(2,2-dimethoxy-ethyl)-amine | 1026652-63-0

• 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-Chloro-7-fluoro-quinoxalin-2-yl)-(2,2-dimethoxy-ethyl)-amine
• 英文别名: 3-chloro-N-(2,2-dimethoxyethyl)-7-fluoroquinoxalin-2-amine
• CAS: 1026652-63-0
• 化学式: C₁₂H₁₃ClFN₃O₂
• 分子量: 285.706
• InChiKey: WGCWCPXRFGUHDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3-Chloro-7-fluoro-quinoxalin-2-yl)-(2,2-dimethoxy-ethyl)-amine 在 氢溴酸 作用下， 生成 8-fluoroimidazo[1,2-a]quinoxalin-4(5H)-one
  参考文献：
  名称：

  Imidazo[1,2-a]quinoxalin-4-amines: A novel class of nonxanthine A1-adenosine receptor antagonists

  摘要：

  The syntheses and A(1) adenosine receptor affinities of a number of imidazo[1,2-alpha]quinoxalin-4-amines are reported. Structure activity relationships within the series and in comparison with other similar tricyclic nonxanthine adenosine antagonists are discussed, leading to a putative common binding mode of these nitrogen-containing heterocycles to A(1) adenosine receptors. Secondary amino compounds displayed the best affinities toward A(1) receptors, while the tertiary amines were almost devoid of activity, thus suggesting a crucial role for the hydrogen bond-forming 4-NH group. Remarkably higher potencies for l-methyl and N-cyclopentyl derivatives were also found. 4-Cyclopentylamino-1-methylimidazo[1,2-alpha]quinoxaline (IRFI 165) is the most potent compound in this series, having K-i(A(1)) = 7.9 nM. It is also provided with a good A(1) selectivity both versus A(2a) and A(3) subtypes and was selected for further pharmacological studies. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80019-1
• 作为产物：
  描述：

  4-氟-1,2-苯二胺 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 40.0h， 生成 (3-Chloro-7-fluoro-quinoxalin-2-yl)-(2,2-dimethoxy-ethyl)-amine
  参考文献：
  名称：

  Imidazo[1,2-a]quinoxalin-4-amines: A novel class of nonxanthine A1-adenosine receptor antagonists

  摘要：

  The syntheses and A(1) adenosine receptor affinities of a number of imidazo[1,2-alpha]quinoxalin-4-amines are reported. Structure activity relationships within the series and in comparison with other similar tricyclic nonxanthine adenosine antagonists are discussed, leading to a putative common binding mode of these nitrogen-containing heterocycles to A(1) adenosine receptors. Secondary amino compounds displayed the best affinities toward A(1) receptors, while the tertiary amines were almost devoid of activity, thus suggesting a crucial role for the hydrogen bond-forming 4-NH group. Remarkably higher potencies for l-methyl and N-cyclopentyl derivatives were also found. 4-Cyclopentylamino-1-methylimidazo[1,2-alpha]quinoxaline (IRFI 165) is the most potent compound in this series, having K-i(A(1)) = 7.9 nM. It is also provided with a good A(1) selectivity both versus A(2a) and A(3) subtypes and was selected for further pharmacological studies. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80019-1

文献信息

• Imidazo[1,2-a]quinoxalin-4-amines: A novel class of nonxanthine A1-adenosine receptor antagonists
  作者：Stefano Ceccarelli、Alessandra D'Alessandro、Michela Prinzivalli、Sergio Zanarella

  DOI：10.1016/s0223-5234(99)80019-1

  日期：1998.12

  The syntheses and A(1) adenosine receptor affinities of a number of imidazo[1,2-alpha]quinoxalin-4-amines are reported. Structure activity relationships within the series and in comparison with other similar tricyclic nonxanthine adenosine antagonists are discussed, leading to a putative common binding mode of these nitrogen-containing heterocycles to A(1) adenosine receptors. Secondary amino compounds displayed the best affinities toward A(1) receptors, while the tertiary amines were almost devoid of activity, thus suggesting a crucial role for the hydrogen bond-forming 4-NH group. Remarkably higher potencies for l-methyl and N-cyclopentyl derivatives were also found. 4-Cyclopentylamino-1-methylimidazo[1,2-alpha]quinoxaline (IRFI 165) is the most potent compound in this series, having K-i(A(1)) = 7.9 nM. It is also provided with a good A(1) selectivity both versus A(2a) and A(3) subtypes and was selected for further pharmacological studies. (C) Elsevier, Paris.