4'-(4-chlorophenyl)-1'H-1,3'-bipyrrole-2'-carbonylazide | 1146320-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4'-(4-chlorophenyl)-1'H-1,3'-bipyrrole-2'-carbonylazide
• 英文别名: 4-(4-chlorophenyl)-3-pyrrol-1-yl-1H-pyrrole-2-carbonyl azide
• CAS: 1146320-49-1
• 化学式: C₁₅H₁₀ClN₅O
• 分子量: 311.73
• InChiKey: JDISSYVBKMRPTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-(4-chlorophenyl)-1'H-1,3'-bipyrrole-2'-carbonylazide 以 邻二氯苯 为溶剂， 反应 0.5h， 以82%的产率得到1-(4-chlorophenyl)-3,4-dihydro-5H-dipyrrolo[1,2-a:2',3'-e]pyrazin-5-one
  参考文献：
  名称：

  Synthesis of new dipyrrolo- and furopyrrolopyrazinones related to tripentones and their biological evaluation as potential kinases (CDKs1–5, GSK-3) inhibitors

  摘要：

  We herein describe the synthesis of novel dipyrrolo- and furopyrrolopyrazinones related to highly cytotoxic tripentones and to their oximes. The synthetic pathway involved in particular a Curtius rearrangement and a subsequent cyclisation into the title pyrazinones. The biological evaluation towards various cyclin-dependent kinases (CDKs1-5, GSK-3) highlighted a weak inhibitory activity for the oximes whose SAR was studied by a molecular modeling study. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.05.011
• 作为产物：
  描述：

  4'-(4-chlorophenyl)-1'H-1,3'-bipyrrole-2'-carbohydrazide 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 3.0h， 以77%的产率得到4'-(4-chlorophenyl)-1'H-1,3'-bipyrrole-2'-carbonylazide
  参考文献：
  名称：

  Synthesis of new dipyrrolo- and furopyrrolopyrazinones related to tripentones and their biological evaluation as potential kinases (CDKs1–5, GSK-3) inhibitors

  摘要：

  We herein describe the synthesis of novel dipyrrolo- and furopyrrolopyrazinones related to highly cytotoxic tripentones and to their oximes. The synthetic pathway involved in particular a Curtius rearrangement and a subsequent cyclisation into the title pyrazinones. The biological evaluation towards various cyclin-dependent kinases (CDKs1-5, GSK-3) highlighted a weak inhibitory activity for the oximes whose SAR was studied by a molecular modeling study. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.05.011