1H-吡唑并[3,4-b]吡啶-3-甲胺 | 1155846-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 中文名称: 1H-吡唑并[3,4-b]吡啶-3-甲胺
• 英文名称: 3-(aminomethyl)-1H-pyrazolo[3,4-b]pyridine
• 英文别名: 3-Aminomethyl-1H-pyrazolo[3,4-B]pyridine；2H-pyrazolo[3,4-b]pyridin-3-ylmethanamine
• CAS: 1155846-90-4
• 化学式: C₇H₈N₄
• mdl: MFCD17016024
• 分子量: 148.167
• InChiKey: RPCRJEFBBHEMAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-吡唑并[3,4-b]吡啶-3-甲胺 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 生成 2-(4-(1-((1H-pyrazolo[3,4-b]pyridin-3-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)-1H-pyrazol-1-yl)ethanol
  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：

  3-甲基-1H-吡唑并[3,4-b]吡啶 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 偶氮二异丁腈 、 三苯基膦 作用下， 以 四氢呋喃 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1H-吡唑并[3,4-b]吡啶-3-甲胺
  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

• [EN] CERTAIN TRIAZOLOPYRIDINES AND TRIAZOLOPYRAZINES, COMPOSITIONS THEREOF AND METHODS OF USE THEREFOR<br/>[FR] CERTAINES TRIAZOLOPYRIDINES ET TRIAZOLOPYRAZINES, LEURS COMPOSITIONS ET LEURS PROCEDES D'UTILISATION
  申请人：HUTCHISON MEDIPHARMA LTD

  公开号：WO2011079804A1

  公开（公告）日：2011-07-07

  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：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。
• NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
  申请人：Tucker Thomas J.

  公开号：US20100256181A1

  公开（公告）日：2010-10-07

  Heteroaromatic compounds of Formula (I) are HIV reverse transcriptase inhibitors, wherein ring A is: (ii-a), (ii-b), (ii-c), (ii-d), or (ii-e); and wherein n, L, M, U, X, Y, Z, R E , R F , R 1 , R 2A , R 2B , R 2C , R 3 , R 8 , R 9 and R 10 are defined herein. The compounds of Formula I and their pharmaceutically acceptable salts and prodrugs are useful in the inhibition of HIV reverse transcriptase, the prophylaxis and treatment of infection by HIV and in the prophylaxis, delay in the onset or progression, and treatment of AIDS. The compounds and their salts and prodrugs can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  公式（I）的杂环芳香化合物是HIV反转录酶抑制剂，其中环A为：（ii-a）、（ii-b）、（ii-c）、（ii-d）或（ii-e）；其中n、L、M、U、X、Y、Z、RE、RF、R1、R2A、R2B、R2C、R3、R8、R9和R10的定义见本文。公式I的化合物及其药学上可接受的盐和前药在抑制HIV反转录酶、预防和治疗HIV感染以及预防、延迟发病或进展和治疗艾滋病方面有用。这些化合物及其盐和前药可作为药物组成部分，可与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。
• Non-nucleoside reverse transcriptase inhibitors
  申请人：Tucker Thomas J.

  公开号：US08404856B2

  公开（公告）日：2013-03-26

  Heteroaromatic compounds of Formula (I) are HIV reverse transcriptase inhibitors, wherein ring A is: (ii-a), (ii-b), (ii-c), (ii-d), or (ii-e); and wherein n, L, M, U, X, Y, Z, RE, RF, R1, R2A, R2B, R2C, R3, R8, R9 and R10 are defined herein. The compounds of Formula I and their pharmaceutically acceptable salts and prodrugs are useful in the inhibition of HIV reverse transcriptase, the prophylaxis and treatment of infection by HIV and in the prophylaxis, delay in the onset or progression, and treatment of AIDS. The compounds and their salts and prodrugs can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  式(I)的杂环芳香化合物是HIV反转录酶抑制剂，其中环A为：(ii-a)、(ii-b)、(ii-c)、(ii-d)或(ii-e)；其中n、L、M、U、X、Y、Z、RE、RF、R1、R2A、R2B、R2C、R3、R8、R9和R10在此定义。式(I)的化合物及其药学上可接受的盐和前药在HIV反转录酶的抑制、预防和治疗HIV感染以及预防、延迟或治疗艾滋病方面有用。这些化合物及其盐和前药可用作制药组合物中的成分，可选择与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。