{5-[4-((E)-2-Pyridin-4-yl-vinyl)-pyridin-3-yl]-[1,3,4]oxadiazol-2-yl}-(3-trifluoromethyl-phenyl)-amine | 883557-32-2

• 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: {5-[4-((E)-2-Pyridin-4-yl-vinyl)-pyridin-3-yl]-[1,3,4]oxadiazol-2-yl}-(3-trifluoromethyl-phenyl)-amine
• CAS: 883557-32-2
• 化学式: C₂₁H₁₄F₃N₅O
• 分子量: 409.37
• InChiKey: SQWGMRCEFOUQHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  76.73
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  {5-[4-((E)-2-Pyridin-4-yl-vinyl)-pyridin-3-yl]-[1,3,4]oxadiazol-2-yl}-(3-trifluoromethyl-phenyl)-amine 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 生成 5-{4-[2-(pyridin-4-yl)ethyl]pyridin-3-yl}-N-[3-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  Inhibitors of VEGF receptors-1 and -2 based on the 2-((pyridin-4-yl)ethyl)pyridine template

  摘要：

  We have developed a series of novel potent ((pyridin-4-yl)ethyl)pyridine derivatives active against kinases VEGFR-1 and -2. Both specific and dual ATP-competitive inhibitors of VEGFR-2 were identified. Kinase selectivity could be controlled by varying the arylamino substituent at the 1,3,4-oxadiazole ring. The most specific molecules displayed >10-fold selectivity for VEGFR-2 over VEGFR-1. Compound activities in vitro and in cell-based assays (IC50 < 100 nM) were similar to those of reported clinical and development candidates, including PTK787 (Vatalanib(TM)). High permeability of active compounds across the Caco-2 cell monolayer (>30 x 10(-5) cm/min) is indicative of their potential for intestinal absorption upon oral administration. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.090
• 作为产物：
  描述：

  阿尔法,阿尔法,阿尔法位-三氟-间-甲苯异硫氰 在 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 {5-[4-((E)-2-Pyridin-4-yl-vinyl)-pyridin-3-yl]-[1,3,4]oxadiazol-2-yl}-(3-trifluoromethyl-phenyl)-amine
  参考文献：
  名称：

  Inhibitors of VEGF receptors-1 and -2 based on the 2-((pyridin-4-yl)ethyl)pyridine template

  摘要：

  We have developed a series of novel potent ((pyridin-4-yl)ethyl)pyridine derivatives active against kinases VEGFR-1 and -2. Both specific and dual ATP-competitive inhibitors of VEGFR-2 were identified. Kinase selectivity could be controlled by varying the arylamino substituent at the 1,3,4-oxadiazole ring. The most specific molecules displayed >10-fold selectivity for VEGFR-2 over VEGFR-1. Compound activities in vitro and in cell-based assays (IC50 < 100 nM) were similar to those of reported clinical and development candidates, including PTK787 (Vatalanib(TM)). High permeability of active compounds across the Caco-2 cell monolayer (>30 x 10(-5) cm/min) is indicative of their potential for intestinal absorption upon oral administration. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.090