3-ethoxy-6-iodo-1-(4-methoxybenzyl)quinolin-2(1H)-one | 1627095-04-8

• 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: 3-ethoxy-6-iodo-1-(4-methoxybenzyl)quinolin-2(1H)-one
• CAS: 1627095-04-8
• 化学式: C₁₉H₁₈INO₃
• 分子量: 435.261
• InChiKey: ZPVPKQLKYCTZGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-bromo-1-(4-methoxybenzyl)-6-nitroquinolin-2(1H)-one 在 盐酸 、 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 反应 1.58h， 生成 3-bromo-6-ethoxy-1-(4-methoxybenzyl)quinolin-2(1H)-one 、 3-ethoxy-6-iodo-1-(4-methoxybenzyl)quinolin-2(1H)-one
  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