7-[5-chloro-4-(3,5-dimethylpyridin-2-yl)pyridin-2-yl]-N-pyridin-3-yl-6,8-dihydro-5H-imidazo[1,2-a]pyrazine-2-carboxamide | 1608503-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 7-[5-chloro-4-(3,5-dimethylpyridin-2-yl)pyridin-2-yl]-N-pyridin-3-yl-6,8-dihydro-5H-imidazo[1,2-a]pyrazine-2-carboxamide
• CAS: 1608503-38-3
• 化学式: C₂₄H₂₂ClN₇O
• 分子量: 459.938
• InChiKey: BPHYGHBTVBYLRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,6,7,8-四氢咪唑并[1,2-a]吡嗪-2-甲酸乙酯 在 N,N-二异丙基乙胺 、 cesium fluoride 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 7-[5-chloro-4-(3,5-dimethylpyridin-2-yl)pyridin-2-yl]-N-pyridin-3-yl-6,8-dihydro-5H-imidazo[1,2-a]pyrazine-2-carboxamide
  参考文献：
  名称：

  Scaffold hopping approach to a new series of smoothened antagonists

  摘要：

  The hedgehog (Hh) signaling pathway is a key regulator during embryonic development, while in adults, it has limited functions such as stem cell maintenance and tissue repair. The aberrant activity of the Hh signaling in adults has been linked to numerous human cancers. Inhibition of Hh signaling therefore represents a promising approach toward novel anticancer therapies. The Smoothened (Smo) receptor mediates Hh signaling. Here we report a new series of Smo antagonists which were obtained by a scaffold hopping strategy. Compounds from this new scaffold demonstrated decent inhibition of Hh pathway signaling. The new scaffold can serve as a starting point for further optimization. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.079

文献信息

• Scaffold hopping approach to a new series of smoothened antagonists
  作者：Wenfeng Lu、Delong Geng、Zhijian Sun、Zhaohui Yang、Haikuo Ma、Jiyue Zheng、Xiaohu Zhang

  DOI：10.1016/j.bmcl.2014.03.079

  日期：2014.5

  The hedgehog (Hh) signaling pathway is a key regulator during embryonic development, while in adults, it has limited functions such as stem cell maintenance and tissue repair. The aberrant activity of the Hh signaling in adults has been linked to numerous human cancers. Inhibition of Hh signaling therefore represents a promising approach toward novel anticancer therapies. The Smoothened (Smo) receptor mediates Hh signaling. Here we report a new series of Smo antagonists which were obtained by a scaffold hopping strategy. Compounds from this new scaffold demonstrated decent inhibition of Hh pathway signaling. The new scaffold can serve as a starting point for further optimization. (C) 2014 Elsevier Ltd. All rights reserved.