2-(3,5-bis(trifluoromethyl)phenyl)-2-((4-(2-fluorophenyl)pyridin-3-yl)methylamino)acetonitrile | 1491169-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(3,5-bis(trifluoromethyl)phenyl)-2-((4-(2-fluorophenyl)pyridin-3-yl)methylamino)acetonitrile
• 英文别名: 2-[3,5-Bis(trifluoromethyl)phenyl]-2-[[4-(2-fluorophenyl)pyridin-3-yl]methylamino]acetonitrile；2-[3,5-bis(trifluoromethyl)phenyl]-2-[[4-(2-fluorophenyl)pyridin-3-yl]methylamino]acetonitrile
• CAS: 1491169-34-6
• 化学式: C₂₂H₁₄F₇N₃
• 分子量: 453.362
• InChiKey: JHROTYQIVZBEAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.7
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(3,5-bis(trifluoromethyl)phenyl)-2-((4-(2-fluorophenyl)pyridin-3-yl)methylamino)acetonitrile 、 丙醛 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 120.0h， 以44%的产率得到2-(3,5-bis(trifluoromethyl)phenyl)-2-(((4-(2-fluorophenyl)pyridin-3-yl)methyl)(propyl)amino)acetonitrile
  参考文献：
  名称：

  Design, synthesis and biological evaluation of a novel class of potent TGR5 agonists based on a 4-phenyl pyridine scaffold

  摘要：

  TGR5, a GPCR, is involved in energy and glucose homeostasis, and as such, is a target for the treatment of diabetes, obesity and other metabolic syndromes. A new class of TGR5 agonists based on a 4-phenyl pyridine scaffold was designed, synthesized and evaluated in vitro and in vivo. Extensive structure activity relationship studies are reported herein. The most potent compounds 15a, 18b and 18c showed comparable activity with the lead compound 2. 15a had the best potency in vitro but displayed an pharmacokinetic profile and was found to be ineffective during an oral glucose tolerance test in imprinting control region mice at a dose of 50 mg/kg. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.050
• 作为产物：
  描述：

  4-氯吡啶-3-羧酸乙酯盐酸盐 在 四(三苯基膦)钯 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 三乙酰氧基硼氢化钠 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 37.5h， 生成 2-(3,5-bis(trifluoromethyl)phenyl)-2-((4-(2-fluorophenyl)pyridin-3-yl)methylamino)acetonitrile
  参考文献：
  名称：

  Design, synthesis and biological evaluation of a novel class of potent TGR5 agonists based on a 4-phenyl pyridine scaffold

  摘要：

  TGR5, a GPCR, is involved in energy and glucose homeostasis, and as such, is a target for the treatment of diabetes, obesity and other metabolic syndromes. A new class of TGR5 agonists based on a 4-phenyl pyridine scaffold was designed, synthesized and evaluated in vitro and in vivo. Extensive structure activity relationship studies are reported herein. The most potent compounds 15a, 18b and 18c showed comparable activity with the lead compound 2. 15a had the best potency in vitro but displayed an pharmacokinetic profile and was found to be ineffective during an oral glucose tolerance test in imprinting control region mice at a dose of 50 mg/kg. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.050