7,8-dichloro-1-methylimidazo[1,2-a]quinoxalin-4(5H)-one | 191349-77-6

• 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: 7,8-dichloro-1-methylimidazo[1,2-a]quinoxalin-4(5H)-one
• 英文别名: 7,8-dichloro-1-methyl-5H-imidazo[1,2-a]quinoxalin-4-one
• CAS: 191349-77-6
• 化学式: C₁₁H₇Cl₂N₃O
• 分子量: 268.102
• InChiKey: AGGLMDATQIKJTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7,8-dichloro-1-methylimidazo[1,2-a]quinoxalin-4(5H)-one 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 生成 4,7,8-Trichloro-1-methylimidazo[1,2-a]quinoxaline
  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：

  2,3,6,7-四氯喹喔啉 在 硫酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 7,8-dichloro-1-methylimidazo[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

文献信息

• US6124287
  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：EP0865442A1

  公开（公告）日：1998-09-23
• 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
• [EN] IMIDAZO[1,2-a]QUINOXALIN-4-AMINES ACTIVE AS ADENOSINE ANTAGONISTS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS THEREOF<br/>[FR] IMIDAZO[1,2-a]QUINOXALINE-4-AMINES EFFICACES EN TANT QU'ANTAGONISTES D'ADENOSINE, PROCEDE SERVANT A LES PREPARER ET LEURS COMPOSITIONS PHARMACEUTIQUES
  申请人：BIOMEDICA FOSCAMA INDUSTRIA CHIMICO-FARMACEUTICA S.P.A.

  公开号：WO1997019079A1

  公开（公告）日：1997-05-29

  (EN) There are described imidazo[1,2-a]quinoxalin-4-amines derivatives of formula (I) and salt thereof active as adenosine antagonists and a process for their preparation and pharmaceutical compositions containing them as therapeutically active compounds for psychiatric and neurological disorders of the central nervous system.(FR) L'invention concerne des dérivés d'imidazo[1,2-a]quinoxaline-4-amines représentés par la formule (I), ainsi que leur sel, efficaces en tant qu'antagonistes d'adénosine, un procédé servant à les préparer et des compositions pharmaceutiques les contenant en tant que composés efficaces sur le plan thérapeutique contre des maladies psychiatriques et neurologiques du système nerveux central.