5-(pyrazin-2-yl)-pyrazino[1,2-a]pyrrolo[2,3-b]quinoxaline | 1346227-97-1

• 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: 5-(pyrazin-2-yl)-pyrazino[1,2-a]pyrrolo[2,3-b]quinoxaline
• 英文别名: 17-Pyrazin-2-yl-2,9,11,14-tetrazatetracyclo[8.7.0.03,8.011,16]heptadeca-1,3,5,7,9,12,14,16-octaene
• CAS: 1346227-97-1
• 化学式: C₁₇H₁₀N₆
• 分子量: 298.307
• InChiKey: CNTXWAJYLXMMPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-甲基吡嗪 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 5-(pyrazin-2-yl)-pyrazino[1,2-a]pyrrolo[2,3-b]quinoxaline
  参考文献：
  名称：

  Fused pyrazino[2,3-b]indolizine and indolizino[2,3-b]quinoxaline derivatives; synthesis, structures, and properties

  摘要：

  The synthesis of six new compounds incorporating either a pyrazino[2,3-b]indolizine or indolizino[2,3-b] quinoxaline core are reported in good yield (58-87%). The intermediates for the key cyclization reaction for one set of compounds (5a-c), with a sterically demanding 3,5-dimethylpyrazole group in the 5-position of the core, were found to be mono-substituted. These intermediates could be isolated and cyclized by heating under acid-catalyzed conditions. To further demonstrate the versatility of the chemistry, compounds 6a-c were synthesized in 58-68% yields. Compounds 5a-c are non-planar in solution and the solid-state, while 6a-c have close to planar conformations, pointing to weak hydrogen bonds between the acidic C-Hs and the adjacent azine nitrogen atoms. The cytotoxicity of the six newly synthesized and three previously prepared compounds was assessed against a human glioblastoma multiforme cell line. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.133

文献信息

• Fused pyrazino[2,3-b]indolizine and indolizino[2,3-b]quinoxaline derivatives; synthesis, structures, and properties
  作者：Witold M. Bloch、Stephanie M. Derwent-Smith、Fatiah Issa、Jonathan C. Morris、Louis M. Rendina、Christopher J. Sumby

  DOI：10.1016/j.tet.2011.09.133

  日期：2011.12

  The synthesis of six new compounds incorporating either a pyrazino[2,3-b]indolizine or indolizino[2,3-b] quinoxaline core are reported in good yield (58-87%). The intermediates for the key cyclization reaction for one set of compounds (5a-c), with a sterically demanding 3,5-dimethylpyrazole group in the 5-position of the core, were found to be mono-substituted. These intermediates could be isolated and cyclized by heating under acid-catalyzed conditions. To further demonstrate the versatility of the chemistry, compounds 6a-c were synthesized in 58-68% yields. Compounds 5a-c are non-planar in solution and the solid-state, while 6a-c have close to planar conformations, pointing to weak hydrogen bonds between the acidic C-Hs and the adjacent azine nitrogen atoms. The cytotoxicity of the six newly synthesized and three previously prepared compounds was assessed against a human glioblastoma multiforme cell line. (C) 2011 Elsevier Ltd. All rights reserved.