3-(phenylethynyl)-2-(2-(pyridin-2-yl)ethoxy)pyrido[3,2-b]pyrazine | 1025014-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶吡嗪类
• 英文名称: 3-(phenylethynyl)-2-(2-(pyridin-2-yl)ethoxy)pyrido[3,2-b]pyrazine
• 英文别名: DGG-954；3-(2-phenylethynyl)-2-(2-pyridin-2-ylethoxy)pyrido[2,3-b]pyrazine
• CAS: 1025014-77-0
• 化学式: C₂₂H₁₆N₄O
• 分子量: 352.395
• InChiKey: MYVNMLLQYATQPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3-二氨基吡啶 在 盐酸 、 copper(l) iodide 、 氯化亚砜 、 palladium diacetate 、 sodium hydride 、 三乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 作用下， 以 四氢呋喃 、 氯仿 、 水 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 59.33h， 生成 3-(phenylethynyl)-2-(2-(pyridin-2-yl)ethoxy)pyrido[3,2-b]pyrazine
  参考文献：
  名称：

  A novel 3-arylethynyl-substituted pyrido[2,3,-b]pyrazine derivatives and pharmacophore model as Wnt2/β-catenin pathway inhibitors in non-small-cell lung cancer cell lines

  摘要：

  We developed Wnt/beta-catenin inhibitors by identifying 13 number of 3-arylethynyl-substituted pyrido[2,3,-b] pyrazine derivatives that were able to inhibit the Wnt/b-catenin signal pathway and cancer cell proliferation. In the optimization process, a series of 2,3,6-trisubstituted pyrido[2,3,-b] pyrazine core skeletons showed were shown to higher activity than 2,3,6-trisubstituted quinoxaline's and thus hold promise for use as potential small-molecule inhibitors of the Wnt/beta-catenin signal pathway in non-small-cell lung cancer cell (NSCLC) lines. And we have studied the pharmacophore mapping for compound 954, which presented the highest activity with a fit value of 2.81. The pharmacophore mapping for the compounds including 954, pyrido[2,3,-b] pyrazine core had hydrogen-bond acceptor site and hydrophobic center roles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.028

文献信息

• US20140255426A1
  申请人：——

  公开号：US20140255426A1

  公开（公告）日：2014-09-11
• A novel 3-arylethynyl-substituted pyrido[2,3,-b]pyrazine derivatives and pharmacophore model as Wnt2/β-catenin pathway inhibitors in non-small-cell lung cancer cell lines
  作者：Young-Dae Gong、Mi-Sook Dong、Sang-Bum Lee、Nayeon Kim、Mi-Seon Bae、Nam-Sook Kang

  DOI：10.1016/j.bmc.2011.07.028

  日期：2011.9

  We developed Wnt/beta-catenin inhibitors by identifying 13 number of 3-arylethynyl-substituted pyrido[2,3,-b] pyrazine derivatives that were able to inhibit the Wnt/b-catenin signal pathway and cancer cell proliferation. In the optimization process, a series of 2,3,6-trisubstituted pyrido[2,3,-b] pyrazine core skeletons showed were shown to higher activity than 2,3,6-trisubstituted quinoxaline's and thus hold promise for use as potential small-molecule inhibitors of the Wnt/beta-catenin signal pathway in non-small-cell lung cancer cell (NSCLC) lines. And we have studied the pharmacophore mapping for compound 954, which presented the highest activity with a fit value of 2.81. The pharmacophore mapping for the compounds including 954, pyrido[2,3,-b] pyrazine core had hydrogen-bond acceptor site and hydrophobic center roles. (C) 2011 Elsevier Ltd. All rights reserved.