N-(3-((1-(4-methoxybenzyl)-2-oxo-6-ureido-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide | 1616393-08-8

• 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-((1-(4-methoxybenzyl)-2-oxo-6-ureido-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide
• CAS: 1616393-08-8
• 化学式: C₂₉H₃₀N₆O₄
• 分子量: 526.595
• InChiKey: JAAWADWPWMVSHP-UHFFFAOYSA-N

物化性质

• 熔点：
  214-217 °C
• 沸点：
  779.7±60.0 °C(predicted)
• 密度：
  1.417±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  130.72
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(3-((1-(4-methoxybenzyl)-2-oxo-6-ureido-1,2-dihydroquinolin-3-yl)amino)phenyl)pyrrolidine-1-carboxamide 在 三氟甲磺酸 、 三氟乙酸 作用下， 反应 3.0h， 以65%的产率得到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
• 作为产物：
  描述：

  3-bromo-1-(4-methoxybenzyl)-6-nitroquinolin-2(1H)-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 溶剂黄146 、 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 、 叔丁醇 为溶剂， 反应 1.5h， 生成 N-(3-((1-(4-methoxybenzyl)-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