N-(2-(6-cyano-1H-indazol-3-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-N-methylbenzamide

• 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: N-(2-(6-cyano-1H-indazol-3-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-N-methylbenzamide
• 英文别名: N-[2-(6-cyano-1H-indazol-3-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl]-N-methylbenzamide
• 化学式: C₂₃H₁₆N₆O
• 分子量: 392.42
• InChiKey: VWOXCLIHKFHBQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1H-吲唑-6-甲腈 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 溴乙烷 、 碘 、 magnesium 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 34.67h， 生成 N-(2-(6-cyano-1H-indazol-3-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)-N-methylbenzamide
  参考文献：
  名称：

  Identification of novel inhibitors of Aurora A with a 3-(pyrrolopyridin-2-yl)indazole scaffold

  摘要：

  A novel series of 3-(pyrrolopyridin-2-yl)indazole derivatives were synthesized and biologically evaluated for their anti-proliferative effects on five human cancer cell lines. As a result, all of them exhibited vigorous potency against HL60 cell line with IC50 values ranging from singe digital nanomolar to micromolar level. Besides, a majority of them displayed modest to good antiproliferative activities against the other four cell lines, including KB, SMMC-7721, HCT116, and A549. Particularly, compound 2y, as the most distinguished one in this series, demonstrated IC50 values of 8.3 nM and 1.3 nM against HL60 and HCT116 cell lines, respectively. Afterwards, for exploring the molecular target, compounds 2d, 2g and 2y were further selected to evaluate the inhibitory activities against a panel of kinases. Finally, they were identified to be targeting Aurora A kinase with significant selectivity over other kinases, such as CHK1, CDK2, MEK1, GSK3 beta, BRAF, IKK beta and PKC. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.004

文献信息

• Identification of novel inhibitors of Aurora A with a 3-(pyrrolopyridin-2-yl)indazole scaffold
  作者：Pinrao Song、Ming Chen、Xiaodong Ma、Lei Xu、Tao Liu、Yubo Zhou、Yongzhou Hu

  DOI：10.1016/j.bmc.2015.02.004

  日期：2015.4

  A novel series of 3-(pyrrolopyridin-2-yl)indazole derivatives were synthesized and biologically evaluated for their anti-proliferative effects on five human cancer cell lines. As a result, all of them exhibited vigorous potency against HL60 cell line with IC50 values ranging from singe digital nanomolar to micromolar level. Besides, a majority of them displayed modest to good antiproliferative activities against the other four cell lines, including KB, SMMC-7721, HCT116, and A549. Particularly, compound 2y, as the most distinguished one in this series, demonstrated IC50 values of 8.3 nM and 1.3 nM against HL60 and HCT116 cell lines, respectively. Afterwards, for exploring the molecular target, compounds 2d, 2g and 2y were further selected to evaluate the inhibitory activities against a panel of kinases. Finally, they were identified to be targeting Aurora A kinase with significant selectivity over other kinases, such as CHK1, CDK2, MEK1, GSK3 beta, BRAF, IKK beta and PKC. (C) 2015 Elsevier Ltd. All rights reserved.