N-(5,6-dipropylindan-2-yl)-2,2,2-trifluoroacetamide | 1225285-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: N-(5,6-dipropylindan-2-yl)-2,2,2-trifluoroacetamide
• CAS: 1225285-19-7
• 化学式: C₁₇H₂₂F₃NO
• 分子量: 313.363
• InChiKey: NWETVQXDETWFRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(5,6-dipropylindan-2-yl)-2,2,2-trifluoroacetamide 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以28%的产率得到2-amino-5,6-di-n-propylindan
  参考文献：
  名称：

  The Identification of Indacaterol as an Ultralong-Acting Inhaled β₂-Adrenoceptor Agonist

  摘要：

  Following a lipophilicity-based hypothesis, an 8-hydroxyquinolinone 2-aminoindan derived series of beta(2)-adrenoceptor agonists have been prepared and evaluated for their potential as inhaled ultralong-acting bronchodilators. Determination of their activities at the human beta(2)-adrenoceptor receptor showed symmetrical substitution of the 2-aminoindan moiety at the 5- and 6-positions delivered the targeted intermediate potency and intrinsic-efficacy profiles relative to a series of clinical reference beta(2)-adrenoceptor agonists. Further assessment with an in vitro superfused electrically stimulated guinea-pig tracheal-strip assay established the onset and duration of action time courses, which could be rationalized by considering the lipophilicity, potency, and intrinsic efficacy of the compounds. From these studies the 5,6-diethylindan analogue indacaterol 1c was shown to possess a unique profile of combining a rapid onset of action with a long duration of action. Further in vivo profiling of 1c supported the long duration of action and a wide therapeutic index following administration to the lung, which led to the compound being selected as a development candidate.

  DOI：

  10.1021/jm100068m
• 作为产物：
  描述：

  5-n-propyl-6-(1-propenyl)-2-aminoindan trifluoroacetamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 19.0~22.0 ℃ 、101.33 kPa 条件下， 以90%的产率得到N-(5,6-dipropylindan-2-yl)-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  The Identification of Indacaterol as an Ultralong-Acting Inhaled β₂-Adrenoceptor Agonist

  摘要：

  Following a lipophilicity-based hypothesis, an 8-hydroxyquinolinone 2-aminoindan derived series of beta(2)-adrenoceptor agonists have been prepared and evaluated for their potential as inhaled ultralong-acting bronchodilators. Determination of their activities at the human beta(2)-adrenoceptor receptor showed symmetrical substitution of the 2-aminoindan moiety at the 5- and 6-positions delivered the targeted intermediate potency and intrinsic-efficacy profiles relative to a series of clinical reference beta(2)-adrenoceptor agonists. Further assessment with an in vitro superfused electrically stimulated guinea-pig tracheal-strip assay established the onset and duration of action time courses, which could be rationalized by considering the lipophilicity, potency, and intrinsic efficacy of the compounds. From these studies the 5,6-diethylindan analogue indacaterol 1c was shown to possess a unique profile of combining a rapid onset of action with a long duration of action. Further in vivo profiling of 1c supported the long duration of action and a wide therapeutic index following administration to the lung, which led to the compound being selected as a development candidate.

  DOI：

  10.1021/jm100068m