5-[(5-bromotriazolo[4,5-b]pyrazin-3-yl)methyl]-1H-thieno[3,2-c]pyrazole | 1313723-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 5-[(5-bromotriazolo[4,5-b]pyrazin-3-yl)methyl]-1H-thieno[3,2-c]pyrazole
• CAS: 1313723-41-9
• 化学式: C₁₀H₆BrN₇S
• 分子量: 336.175
• InChiKey: BTYBBOZRYLSQCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-甲基-4-(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷-2-基)-1H-吡唑 、 5-[(5-bromotriazolo[4,5-b]pyrazin-3-yl)methyl]-1H-thieno[3,2-c]pyrazole 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 5-[[5-(1-methylpyrazol-4-yl)triazolo[4,5-b]pyrazin-3-yl]methyl]-1H-thieno[3,2-c]pyrazole
  参考文献：
  名称：

  Discovery of (S)-1-(1-(Imidazo[1,2-a]pyridin-6-yl)ethyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (Volitinib) as a Highly Potent and Selective Mesenchymal–Epithelial Transition Factor (c-Met) Inhibitor in Clinical Development for Treatment of Cancer

  摘要：

  HGF/c-Met signaling has been implicated in human cancers. Herein we describe the invention of a series of novel triazolopyrazine c-Met inhibitors. The structure activity relationship of these compounds was investigated, leading to the identification of compound 28, which demonstrated favorable pharmacokinetic properties in mice and good antitumor activities in the human glioma xenograft model in athymic nude mice.

  DOI：

  10.1021/jm500510f
• 作为产物：
  描述：

  5-甲基噻吩-2-羧酸甲酯 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 硫酸 、 叠氮磷酸二苯酯 、 palladium 10% on activated carbon 、 氢气 、 硝酸 、 potassium acetate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 51.0h， 生成 5-[(5-bromotriazolo[4,5-b]pyrazin-3-yl)methyl]-1H-thieno[3,2-c]pyrazole
  参考文献：
  名称：

  Discovery of (S)-1-(1-(Imidazo[1,2-a]pyridin-6-yl)ethyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (Volitinib) as a Highly Potent and Selective Mesenchymal–Epithelial Transition Factor (c-Met) Inhibitor in Clinical Development for Treatment of Cancer

  摘要：

  HGF/c-Met signaling has been implicated in human cancers. Herein we describe the invention of a series of novel triazolopyrazine c-Met inhibitors. The structure activity relationship of these compounds was investigated, leading to the identification of compound 28, which demonstrated favorable pharmacokinetic properties in mice and good antitumor activities in the human glioma xenograft model in athymic nude mice.

  DOI：

  10.1021/jm500510f

文献信息

• CERTAIN TRIAZOLOPYRIDINES AND TRIAZOLOPYRAZINES, COMPOSITIONS THEREOF AND METHODS OF USE THEREFOR
  申请人：SU Wei-Guo

  公开号：US20120245178A1

  公开（公告）日：2012-09-27

  Provided are certain triazolopyridines and triazolopyrazines, compositions thereof and methods of use therefor.

  提供了某些三唑吡啶和三唑吡嗪，以及它们的组成物和使用方法。
• CERTAIN TRIAZOLOPYRIDINES AND TRIAZOLOPYRAZINES, COMPOSITIONS THEREOF AND METHODS OF USE THEREFOR
  申请人：Su Wei-Guo

  公开号：US20120264739A1

  公开（公告）日：2012-10-18

  Provided are certain triazolopyridines and triazolopyrazines, compositions thereof and methods of use therefor.

  提供了某些三唑并吡啶和三唑并嘧啶，以及它们的组成物和使用方法。
• CERTAIN TRIAZOLOPYRIDINES, COMPOSITIONS THEREOF AND THEIR USE IN THE TREATMENT OF CANCER.
  申请人：Hutchison Medipharma Limited

  公开号：EP2966075A1

  公开（公告）日：2016-01-13

  Provided are certain triazolopyridines, compositions thereof and their use in the treatment of cancer.

  本文提供了某些三唑并吡啶、其组合物及其在治疗癌症中的用途。
• SYNTHETIC INTERMEDIATE USEFUL IN THE PREPARATION OF TRIAZOLOPYRIDINE C-MET INHIBITORS
  申请人：Hutchison Medipharma Limited

  公开号：EP3511330A1

  公开（公告）日：2019-07-17

  The specification relates to a compound of the formula: and salt thereof.

  本说明书涉及一种式化合物： 及其盐。
• Certain triazolopyridines and triazolopyrazines, compositions thereof and methods of use therefor
  申请人：Hutchison Medipharma Limited

  公开号：US10946014B2

  公开（公告）日：2021-03-16

  Provided are certain triazolopyridines and triazolopyrazines, compositions thereof and methods of use therefor.

  本文提供了某些三唑并吡啶和三唑并吡嗪、其组合物及其使用方法。