1-[4-(trifluoromethyl)benzoyl]azulene-6-carboxylic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-(trifluoromethyl)benzoyl]azulene-6-carboxylic acid
• 英文别名: 1-[4-(Trifluoromethyl)benzoyl]azulene-6-carboxylic acid
• 化学式: C₁₉H₁₁F₃O₃
• 分子量: 344.29
• InChiKey: AIHVJYFGVPIWAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-azulenylcarbaldehyde 在 Oxone 、 potassium carbonate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.25h， 生成 1-[4-(trifluoromethyl)benzoyl]azulene-6-carboxylic acid
  参考文献：
  名称：

  Azulene-based compounds for targeting orexin receptors

  摘要：

  A library of 70 000 synthetically accessible azulene-based compounds was virtually screened at the OX2 receptor. Based on the results, a series of azulene derivatives was synthesized and the binding to and activation of both orexin receptor subtypes were assessed. Two most promising binders were determined to have inhibition constants in the 3-9 mu M range and two other compounds showed weak OX2 receptor agonism. Furthermore, three compounds exhibited a concentration-dependent potentiation of the response to orexin-A at the OX1 but not the OX2 receptors. Altogether this data opens new approaches for further development of antagonists, agonists, and potentiators of orexin response based on the azulene scaffold. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.040

文献信息

• Azulene-based compounds for targeting orexin receptors
  作者：Teppo O. Leino、Ainoleena Turku、Jari Yli-Kauhaluoma、Jyrki P. Kukkonen、Henri Xhaard、Erik A.A. Wallén

  DOI：10.1016/j.ejmech.2018.07.040

  日期：2018.9

  A library of 70 000 synthetically accessible azulene-based compounds was virtually screened at the OX2 receptor. Based on the results, a series of azulene derivatives was synthesized and the binding to and activation of both orexin receptor subtypes were assessed. Two most promising binders were determined to have inhibition constants in the 3-9 mu M range and two other compounds showed weak OX2 receptor agonism. Furthermore, three compounds exhibited a concentration-dependent potentiation of the response to orexin-A at the OX1 but not the OX2 receptors. Altogether this data opens new approaches for further development of antagonists, agonists, and potentiators of orexin response based on the azulene scaffold. (C) 2018 Elsevier Masson SAS. All rights reserved.