N-(3-((2-oxo-6-ureido-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide | 1616393-24-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(3-((2-oxo-6-ureido-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide
• 英文别名: N-[3-[[6-(carbamoylamino)-2-oxo-1H-quinolin-3-yl]amino]phenyl]pyrrolidine-1-carboxamide
• CAS: 1616393-24-8
• 化学式: C₂₁H₂₂N₆O₃
• 分子量: 406.444
• InChiKey: VPEGWANCCFGPQA-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  739.167±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.482±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-硝基-2(1h)-喹啉酮 在 sodium bromate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三氟甲磺酸 、 氢溴酸 、 potassium carbonate 、 溶剂黄146 、 三氟乙酸 、 锌 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 8.5h， 生成 N-(3-((2-oxo-6-ureido-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted 3-anilino-quinolin-2(1H)-ones as PDK1 inhibitors

  摘要：

  PDK1 is an important regulator of the PI3K/Akt pathway, which has been found frequently activated in a large number of human cancers. Herein we described the preparation of novel substituted 3-anilino-quinolin-2(1H)-ones as PDK1 inhibitors. The synthesis is based around a Buchwald-Hartwig cross-coupling of various 3-bromo-6-substituted-quinolin-2(1H)-ones with three different functionalised anilines. The modular nature of the designed synthesis allowed access to a series of novel inhibitors through derivatisation of a late-stage intermediate. All compounds were screened against isolated PDK1 enzyme, with modest inhibition observed.

  DOI：

  10.1016/j.bmc.2014.04.037

文献信息

• Synthesis and biological evaluation of substituted 3-anilino-quinolin-2(1H)-ones as PDK1 inhibitors
  作者：Nathan J. O’Brien、Martin Brzozowski、David J.D. Wilson、Leslie W. Deady、Belinda M. Abbott

  DOI：10.1016/j.bmc.2014.04.037

  日期：2014.7

  PDK1 is an important regulator of the PI3K/Akt pathway, which has been found frequently activated in a large number of human cancers. Herein we described the preparation of novel substituted 3-anilino-quinolin-2(1H)-ones as PDK1 inhibitors. The synthesis is based around a Buchwald-Hartwig cross-coupling of various 3-bromo-6-substituted-quinolin-2(1H)-ones with three different functionalised anilines. The modular nature of the designed synthesis allowed access to a series of novel inhibitors through derivatisation of a late-stage intermediate. All compounds were screened against isolated PDK1 enzyme, with modest inhibition observed.