1-(5-bromo-6-ethoxy-1H-indazol-1-yl)ethanone | 1613504-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 1-(5-bromo-6-ethoxy-1H-indazol-1-yl)ethanone
• 英文别名: 1-(5-Bromo-6-ethoxyindazol-1-yl)ethanone
• CAS: 1613504-72-5
• 化学式: C₁₁H₁₁BrN₂O₂
• 分子量: 283.125
• InChiKey: WVLFNLAWJPRPJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-bromo-6-ethoxy-1H-indazol-1-yl)ethanone 在 盐酸 、 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 生成 6-ethoxy-5-(2-trifluoromethylphenyl)-1H-indazole
  参考文献：
  名称：

  Discovery, Optimization, and Biological Evaluation of 5-(2-(Trifluoromethyl)phenyl)indazoles as a Novel Class of Transient Receptor Potential A1 (TRPA1) Antagonists

  摘要：

  A high throughput screening campaign identified 5-(2-chlorophenyl)indazole compound 4 as an antagonist of the transient receptor potential A1 (TRPA1) ion channel with IC50 = 1.23 μM. Hit to lead medicinal chemistry optimization established the SAR around the indazole ring system, demonstrating that a trifluoromethyl group at the 2-position of the phenyl ring in combination with various substituents at the 6-position of the indazole ring greatly contributed to improvements in vitro activity. Further lead optimization resulted in the identification of compound 31, a potent and selective antagonist of TRPA1 in vitro (IC50 = 0.015 μM), which has moderate oral bioavailability in rodents and demonstrates robust activity in vivo in several rodent models of inflammatory pain.

  DOI：

  10.1021/jm401986p
• 作为产物：
  描述：

  4-乙氧基-1-甲基-2-硝基苯 在 N-溴代丁二酰亚胺(NBS) 、 18-冠醚-6 、 palladium on activated charcoal 、 甲酸铵 、 potassium acetate 、 乙酸酐 、 亚硝酸异戊酯 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.5h， 生成 1-(5-bromo-6-ethoxy-1H-indazol-1-yl)ethanone
  参考文献：
  名称：

  Discovery, Optimization, and Biological Evaluation of 5-(2-(Trifluoromethyl)phenyl)indazoles as a Novel Class of Transient Receptor Potential A1 (TRPA1) Antagonists

  摘要：

  A high throughput screening campaign identified 5-(2-chlorophenyl)indazole compound 4 as an antagonist of the transient receptor potential A1 (TRPA1) ion channel with IC50 = 1.23 μM. Hit to lead medicinal chemistry optimization established the SAR around the indazole ring system, demonstrating that a trifluoromethyl group at the 2-position of the phenyl ring in combination with various substituents at the 6-position of the indazole ring greatly contributed to improvements in vitro activity. Further lead optimization resulted in the identification of compound 31, a potent and selective antagonist of TRPA1 in vitro (IC50 = 0.015 μM), which has moderate oral bioavailability in rodents and demonstrates robust activity in vivo in several rodent models of inflammatory pain.

  DOI：

  10.1021/jm401986p