2-phenyl-4-chloroimidazo<1,5-a>quinoxaline | 168210-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-4-chloroimidazo<1,5-a>quinoxaline
• 英文别名: 4-chloro-1-phenylimidazo[1,5-a]quinoxaline
• CAS: 168210-44-4
• 化学式: C₁₆H₁₀ClN₃
• 分子量: 279.728
• InChiKey: OXQJGEIWOMNGSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-chloroimidazo<1,5-a>quinoxaline 在 氨 作用下， 以 异丙醇 为溶剂， 反应 40.0h， 以50%的产率得到2-phenylimidazol<1,5-a>quinoxalin-4-amine
  参考文献：
  名称：

  Synthesis of some tricyclic heteroaromatic systems and their A1 and A2a adenosine binding activity

  摘要：

  The syntheses, A(1) and A(2a) adenosine receptor affinities and structure-activity relationships of some 2-aryl-1,2,4-triazolo[1,5-a]quinoxalines, 2-arylimidazo[1,2-a]quinoxalines, 1-arylimidazo[1,5-a]quinoxalines are reported and compared with that of a previously reported 2-phenylpyrazolo[1,5-a]quinoxaline. The results show that some triazoloquinoxalines are potent and specific A(1) adenosine receptor ligands and that the replacement of either nitrogen at position 1 or 3 of the triazoloquinoxaline moiety with a CH brought about a decrease in affinity at both adenosine receptors.

  DOI：

  10.1016/0223-5234(96)88218-3
• 作为产物：
  描述：

  4,5-dihydro-1-phenylimidazo<1,5-a>quinoxalin-4-one 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 反应 6.0h， 以40%的产率得到2-phenyl-4-chloroimidazo<1,5-a>quinoxaline
  参考文献：
  名称：

  Synthesis of some tricyclic heteroaromatic systems and their A1 and A2a adenosine binding activity

  摘要：

  The syntheses, A(1) and A(2a) adenosine receptor affinities and structure-activity relationships of some 2-aryl-1,2,4-triazolo[1,5-a]quinoxalines, 2-arylimidazo[1,2-a]quinoxalines, 1-arylimidazo[1,5-a]quinoxalines are reported and compared with that of a previously reported 2-phenylpyrazolo[1,5-a]quinoxaline. The results show that some triazoloquinoxalines are potent and specific A(1) adenosine receptor ligands and that the replacement of either nitrogen at position 1 or 3 of the triazoloquinoxaline moiety with a CH brought about a decrease in affinity at both adenosine receptors.

  DOI：

  10.1016/0223-5234(96)88218-3

文献信息

• In vitro and in vivo anti-tumoral activities of imidazo[1,2-a]quinoxaline, imidazo[1,5-a]quinoxaline, and pyrazolo[1,5-a]quinoxaline derivatives
  作者：Georges Moarbess、Carine Deleuze-Masquefa、Vanessa Bonnard、Stéphanie Gayraud-Paniagua、Jean-Rémi Vidal、Françoise Bressolle、Frédéric Pinguet、Pierre-Antoine Bonnet

  DOI：10.1016/j.bmc.2008.05.022

  日期：2008.7.1

  Imidazoquinoxaline and pyrazoloquinoxaline derivatives, analogues of imiquimod, were synthesized, and their in vitro cytotoxic and pharmacodynamic activities were evaluated. In vitro cytotoxicity studies were assessed against melanoma (A375, M4Be, RPMI-7591), colon (LS174T), breast (MCF7), and lymphoma (Raji) human cancer cell lines. In vivo studies were carried out in M4Be xenografted athymic mice. EAPB0103, EAPB0201, EAPB0202, and EAPB0203 showed significant in vitro activities against A375 compared to fotemustine and imiquimod used as references. These compounds were 6-110 and 2-45 times more active than fotemustine and imiquimod, respectively. EAPB0203 bearing phenethyl as substituent at position 1 and methylamine at position 4 showed the highest activity. EAPB0203 has also a more potent cytotoxic activity than imiquimod and fotemustine in M4Be and RPMI-7591 and interesting cytotoxic activity in other tumor cell lines tested. In vivo, EAPB0203 treatment schedules caused a significant decrease in tumor size compared to vehicle control and fotemustine treatments. (c) 2008 Elsevier Ltd. All rights reserved.