N-(3-(2-oxo-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)-5-((2-oxo-6-ureido-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide | 1616393-26-0

• 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-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)-5-((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]-5-[2-oxo-2-(2-piperidin-1-ylethylamino)ethyl]phenyl]pyrrolidine-1-carboxamide
• CAS: 1616393-26-0
• 化学式: C₃₀H₃₈N₈O₄
• 分子量: 574.683
• InChiKey: VRPJCLAEEBSNJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  161
• 氢给体数：
  6
• 氢受体数：
  6

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-2-((2-(piperidin-1-yl)ethyl)amino)ethyl)-5-((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.