5-(2-chlorophenyl)-1H-indazole | 1613504-96-3

• 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: 5-(2-chlorophenyl)-1H-indazole
• CAS: 1613504-96-3
• 化学式: C₁₃H₉ClN₂
• 分子量: 228.681
• InChiKey: WPNNDKHQYVORDG-UHFFFAOYSA-N

物化性质

• 沸点：
  412.5±20.0 °C(predicted)
• 密度：
  1.326±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氯苯基硼酸 、 5-溴吲唑 在 2’-(dimethylamino)-2-biphenylylpalladium(II) chloride dinorbornylphosphine complex 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 5-(2-chlorophenyl)-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

文献信息

• Discovery, Optimization, and Biological Evaluation of 5-(2-(Trifluoromethyl)phenyl)indazoles as a Novel Class of Transient Receptor Potential A1 (TRPA1) Antagonists
  作者：Lisa Rooney、Agnès Vidal、Anne-Marie D’Souza、Nick Devereux、Brian Masick、Valerie Boissel、Ryan West、Victoria Head、Rowan Stringer、Jianmin Lao、Matt J. Petrus、Ardem Patapoutian、Mark Nash、Natalie Stoakley、Moh Panesar、J. Martin Verkuyl、Andrew M. Schumacher、H. Michael Petrassi、David C. Tully

  DOI：10.1021/jm401986p

  日期：2014.6.26

  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.