7-溴-3-三氟甲基-1H-吲唑 | 57631-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 7-溴-3-三氟甲基-1H-吲唑
• 英文名称: 7-bromo-3-trifluoromethyl-1H-indazole
• 英文别名: 7-Bromo-3-(trifluoromethyl)-1H-indazole；7-bromo-3-(trifluoromethyl)-2H-indazole
• CAS: 57631-12-6
• 化学式: C₈H₄BrF₃N₂
• 分子量: 265.032
• InChiKey: DQUKJDLLGPDJMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2,2,2-trifluoro-ethyl)-aniline 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 反应 120.0h， 生成 7-溴-3-三氟甲基-1H-吲唑
  参考文献：
  名称：

  Design and synthesis of pyridine–pyrazolopyridine-based inhibitors of protein kinase B/Akt

  摘要：

  Thr-211 is one of three different amino acid residues in the kinase domain of protein kinase B/Akt as compared to protein kinase A (PKA), a closely related analog in the same AGC family. In an attempt to improve the potency and selectivity of our indazole-pyridine series of Akt inhibitors over PKA, efforts have focused on the incorporation of a chemical functionality to interact with the hydroxy group of Thr-211. Several substituents including an oxygen anion, amino, and nitro groups have been introduced at the C-6 position of the indazole scaffold, leading to a significant drop in Akt potency. Incorporation of a nitrogen atom into the phenyl ring at the same position (i.e., 9f) maintained the Akt activity and, in some cases, improved the selectivity over PKA. The structure-activity relationships of the new pyridine-pyrazolopyridine series of Akt inhibitors and their structural features when bound to PKA are also discussed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.010

文献信息

• Design and synthesis of pyridine–pyrazolopyridine-based inhibitors of protein kinase B/Akt
  作者：Gui-Dong Zhu、Jianchun Gong、Viraj B. Gandhi、Keith Woods、Yan Luo、Xuesong Liu、Ran Guan、Vered Klinghofer、Eric F. Johnson、Vincent S. Stoll、Mulugeta Mamo、Qun Li、Saul H. Rosenberg、Vincent L. Giranda

  DOI：10.1016/j.bmc.2007.01.010

  日期：2007.3

  Thr-211 is one of three different amino acid residues in the kinase domain of protein kinase B/Akt as compared to protein kinase A (PKA), a closely related analog in the same AGC family. In an attempt to improve the potency and selectivity of our indazole-pyridine series of Akt inhibitors over PKA, efforts have focused on the incorporation of a chemical functionality to interact with the hydroxy group of Thr-211. Several substituents including an oxygen anion, amino, and nitro groups have been introduced at the C-6 position of the indazole scaffold, leading to a significant drop in Akt potency. Incorporation of a nitrogen atom into the phenyl ring at the same position (i.e., 9f) maintained the Akt activity and, in some cases, improved the selectivity over PKA. The structure-activity relationships of the new pyridine-pyrazolopyridine series of Akt inhibitors and their structural features when bound to PKA are also discussed. (c) 2007 Elsevier Ltd. All rights reserved.