4-bromo-5-ethyl-2-methylaniline | 1613504-69-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-5-ethyl-2-methylaniline
• CAS: 1613504-69-0
• 化学式: C₉H₁₂BrN
• 分子量: 214.105
• InChiKey: XHHKVZSYLLXIAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-5-ethyl-2-methylaniline 在 四(三苯基膦)钯 、 18-冠醚-6 、 potassium acetate 、 乙酸酐 、 caesium carbonate 、 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 、 氯仿 、 水 、 甲苯 为溶剂， 生成 C₁₈H₁₅F₃N₂O
  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：

  5-乙基-2-甲基苯胺 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以72%的产率得到4-bromo-5-ethyl-2-methylaniline
  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

• Dialkylphenyl compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity
  申请人：Colson Pierre-Jean

  公开号：US20070249675A1

  公开（公告）日：2007-10-25

  This invention relates to compounds of formula I: wherein R 1 and R 2 are as defined in the specification, or a pharmaceutically acceptable salt or solvate or stereoisomer thereof. The invention also relates to pharmaceutical compositions and combinations comprising such compounds, processes and intermediates for preparing such compounds, and methods of using such compound to, for example, treat pulmonary disorders, such as chronic obstructive pulmonary disease and asthma.

  本发明涉及式I的化合物：其中R1和R2如规范中定义，或其药用可接受的盐或溶剂或立体异构体。该发明还涉及包含这类化合物的药物组合物和配方，用于制备这类化合物的过程和中间体，以及使用这类化合物治疗肺部疾病，如慢性阻塞性肺病和哮喘等方法。
• DIALKYLPHENYL COMPOUNDS HAVING BETA2 ADRENERGIC RECEPTOR AGONIST AND MUSCARINIC RECEPTOR ANTAGONIST ACTIVITY
  申请人：Colson Pierre-Jean

  公开号：US20100137603A1

  公开（公告）日：2010-06-03

  This invention relates to compounds of formula I: wherein R 1 and R 2 are as defined in the specification, or a pharmaceutically acceptable salt or solvate or stereoisomer thereof. The invention also relates to pharmaceutical compositions and combinations comprising such compounds, processes and intermediates for preparing such compounds, and methods of using such compound to, for example, treat pulmonary disorders, such as chronic obstructive pulmonary disease and asthma.

  本发明涉及I式化合物： 其中R1和R2如本说明书所定义，或其药学上可接受的盐、溶剂或立体异构体。本发明还涉及包括这种化合物的药物组合物和制备这种化合物的中间体和过程，以及使用这种化合物的方法，例如用于治疗肺部疾病，如慢性阻塞性肺疾病和哮喘。
• DIALKYLPHENYL COMPOUNDS HAVING 2 ADRENERGIC RECEPTOR AGONIST AND MUSCARINIC RECEPTOR ANTAGONIST ACTIVITY
  申请人：Theravance, Inc.

  公开号：EP2010489A2

  公开（公告）日：2009-01-07
• US7524965B2
  申请人：——

  公开号：US7524965B2

  公开（公告）日：2009-04-28
• US7687521B2
  申请人：——

  公开号：US7687521B2

  公开（公告）日：2010-03-30