(2'Z,3'E)-7-aza-1-methylindirubin-3'-oxime | 1202876-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: (2'Z,3'E)-7-aza-1-methylindirubin-3'-oxime
• 英文别名: (2'Z,3'E)-7-aza-N-methylindirubin-3'-oxime
• CAS: 1202876-74-1
• 化学式: C₁₆H₁₂N₄O₂
• 分子量: 292.297
• InChiKey: LNCJGGHWQWLMAT-WROMKANLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  77.82
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (2'Z)-7-aza-1-methylindirubin 在 吡啶 、 盐酸羟胺 作用下， 以100%的产率得到(2'Z,3'E)-7-aza-1-methylindirubin-3'-oxime
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity of 7-Azaindirubin-3′-oxime, a 7-Aza Isostere of the Natural Indirubin Pharmacophore

  摘要：

  The bis-indole alkaloid indirubin and its analogues bear a very interesting natural pharmacophore. They are recognized mainly as kinase inhibitors, but several other activities make them possible candidates for preclinical studies. Based on the previously reported activity of 7-bromoindirubin-3'-oxime and its derivatives, the synthesis of indirubins bearing a heterocyclic nitrogen atom at position 7 was carried out. Herein, we report the first synthesis of 7-azaindirubin-3'-oxime (12) as well as its antiproliferative activity against 57 cancer cell lines and its inhibitory activity against a series of kinases. 7-Azaindirubin (10) and its 3'-oxime derivative (12) showed reduced activity as kinase inhibitors in comparison with other known indirubin derivatives, but antiproliferative activity with a best GI(50) value of 0.77 mu M.

  DOI：

  10.1021/np9003905

文献信息

• Synthesis and Antiproliferative Activity of 7-Azaindirubin-3′-oxime, a 7-Aza Isostere of the Natural Indirubin Pharmacophore
  作者：Marina Kritsanida、Prokopios Magiatis、Alexios-Leandros Skaltsounis、Youyi Peng、Peng Li、Lawrence P. Wennogle

  DOI：10.1021/np9003905

  日期：2009.12.28

  The bis-indole alkaloid indirubin and its analogues bear a very interesting natural pharmacophore. They are recognized mainly as kinase inhibitors, but several other activities make them possible candidates for preclinical studies. Based on the previously reported activity of 7-bromoindirubin-3'-oxime and its derivatives, the synthesis of indirubins bearing a heterocyclic nitrogen atom at position 7 was carried out. Herein, we report the first synthesis of 7-azaindirubin-3'-oxime (12) as well as its antiproliferative activity against 57 cancer cell lines and its inhibitory activity against a series of kinases. 7-Azaindirubin (10) and its 3'-oxime derivative (12) showed reduced activity as kinase inhibitors in comparison with other known indirubin derivatives, but antiproliferative activity with a best GI(50) value of 0.77 mu M.