IRFI 165 | 191349-26-5

• 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: IRFI 165
• 英文别名: 4-cyclopentylamino-1-methylimidazo[1,2-a]quinoxaline；4-(Cyclopentylamino)-1-methylimidazo(1,2-a)quinoxaline；N-cyclopentyl-1-methylimidazo[1,2-a]quinoxalin-4-amine
• CAS: 191349-26-5
• 化学式: C₁₆H₁₈N₄
• 分子量: 266.346
• InChiKey: QRZLMPANXOGORV-UHFFFAOYSA-N

物化性质

• 沸点：
  433.0±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-chloro-3-propargylaminoquinoxaline 在 硫酸氢铵 、 硫酸 、 六甲基二硅氮烷 作用下， 反应 1.0h， 生成 IRFI 165
  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

• US6124287
  申请人：——

  公开号：——

  公开（公告）日：——
• US06124287
  申请人：——

  公开号：——

  公开（公告）日：——
• IMIDAZO[1,2-a]QUINOXALIN-4-AMINES ACTIVE AS ADENOSINE ANTAGONISTS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THEREOF
  申请人：Biomedica Foscama Industria Chimico-Farmaceutica S.p.A.

  公开号：EP0865442B1

  公开（公告）日：2000-07-05
• US6124287A
  申请人：——

  公开号：US6124287A

  公开（公告）日：2000-09-26
• 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.