3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)aniline | 1428155-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)aniline
• 英文别名: 3-[9-(Oxan-2-yl)purin-6-yl]aniline；3-[9-(oxan-2-yl)purin-6-yl]aniline
• CAS: 1428155-06-9
• 化学式: C₁₆H₁₇N₅O
• 分子量: 295.344
• InChiKey: ZMCAVLBEMWLOLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)aniline 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 6.0h， 生成 4-bromo-3-methyl-N-[3-(7H-purin-6-yl)phenyl]benzamide
  参考文献：
  名称：

  Inhibitors of the TAM subfamily of tyrosine kinases: Synthesis and biological evaluation

  摘要：

  The TAM subfamily of Receptor Tyrosine Kinases (RTKs) contains three human proteins of therapeutical interest, Axl, Mer, and Tyro3. Our goal was to design a type II inhibitor specific for this family, i.e. able to interact with the allosteric pocket and with the hinge region of the kinase. We report the synthesis of several series of purine analogues of BMS-777607. The structural diversity of the designed inhibitors was expected to modify the interactions formed in the binding site and consequently to modulate their selectivity profiles. The most potent inhibitor 6g exhibits K(d)s of 39, 42, 65 and 200 nM against Axl, Mer, Met and Tyro3 respectively. Analysis of the affinity of 6g for active and inactive forms of Abl1, an RTK protein that does not belong to the TAM subfamily, together with the binding modes of 6g predicted by docking studies, indicates that 6g displays some selectivity for the TAM family and may act as a type II inhibitor. Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.005
• 作为产物：
  描述：

  3-硝基苯硼酸 在 四(三苯基膦)钯 、 铁粉 、 potassium carbonate 、 氯化铵 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 17.0h， 生成 3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)aniline
  参考文献：
  名称：

  Inhibitors of the TAM subfamily of tyrosine kinases: Synthesis and biological evaluation

  摘要：

  The TAM subfamily of Receptor Tyrosine Kinases (RTKs) contains three human proteins of therapeutical interest, Axl, Mer, and Tyro3. Our goal was to design a type II inhibitor specific for this family, i.e. able to interact with the allosteric pocket and with the hinge region of the kinase. We report the synthesis of several series of purine analogues of BMS-777607. The structural diversity of the designed inhibitors was expected to modify the interactions formed in the binding site and consequently to modulate their selectivity profiles. The most potent inhibitor 6g exhibits K(d)s of 39, 42, 65 and 200 nM against Axl, Mer, Met and Tyro3 respectively. Analysis of the affinity of 6g for active and inactive forms of Abl1, an RTK protein that does not belong to the TAM subfamily, together with the binding modes of 6g predicted by docking studies, indicates that 6g displays some selectivity for the TAM family and may act as a type II inhibitor. Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.005

文献信息

• N-取代苯基酰胺衍生物及其制备方法和用途
  申请人：四川大学

  公开号：CN105837572B

  公开（公告）日：2019-04-19

  本发明属于化学医药领域，具体涉及N‑取代苯基酰胺衍生物及其制备方法和用途。本发明提供了一种N‑取代苯基酰胺衍生物，其结构如式Ⅰ所示。本发明还提供了上述N‑取代苯基酰胺衍生物的制备方法和用途。本发明提供的N‑取代苯基酰胺衍生物，可以选择性地抑制JAK3，为治疗与之相关的疾病，如类风湿关节炎、哮喘、慢性阻塞性肺疾病和肿瘤等提供了新的选择。