4-(4-methoxyphenyl)-3-(1H-pyrrol-1-yl)-2-furoyl azide | 1146320-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)-3-(1H-pyrrol-1-yl)-2-furoyl azide
• 英文别名: 4-(4-Methoxyphenyl)-3-pyrrol-1-ylfuran-2-carbonyl azide
• CAS: 1146320-59-3
• 化学式: C₁₆H₁₂N₄O₃
• 分子量: 308.296
• InChiKey: YXEGPCBGXZCYPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)-3-(1H-pyrrol-1-yl)-2-furoyl azide 以 邻二氯苯 为溶剂， 反应 0.03h， 以70%的产率得到1-(4-methoxyphenyl)furo[2,3-e]pyrrolo[1,2-a]pyrazin-5(4H)-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-methoxyphenyl)-3-(1H-pyrrol-1-yl)-2-furoic acid 在 sodium azide 、 氯甲酸乙酯 、 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以90%的产率得到4-(4-methoxyphenyl)-3-(1H-pyrrol-1-yl)-2-furoyl azide
  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

文献信息

• Synthesis of new dipyrrolo- and furopyrrolopyrazinones related to tripentones and their biological evaluation as potential kinases (CDKs1–5, GSK-3) inhibitors
  作者：Christophe Rochais、Nghia Vu Duc、Elodie Lescot、Jana Sopkova-de Oliveira Santos、Ronan Bureau、Laurent Meijer、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.ejmech.2008.05.011

  日期：2009.2

  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.