6-chloro-8-(naphthalen-2-yl)-9H-purine | 1170069-83-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-chloro-8-(naphthalen-2-yl)-9H-purine
• CAS: 1170069-83-6
• 化学式: C₁₅H₉ClN₄
• 分子量: 280.716
• InChiKey: HNKRHJMDNBUYJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  乙酰胺 、 6-chloro-8-(naphthalen-2-yl)-9H-purine 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 生成 N-(8-naphthalen-2-yl-7H-purin-6-yl)acetamide
  参考文献：
  名称：

  Novel 8-arylated purines as inhibitors of glycogen synthase kinase

  摘要：

  A series of 8-arylated purine derivatives bearing either an aniline or an alkyl amide at position 6 were found to inhibit glycogen synthase kinase-3, with good selectivity over ten kinases. Molecular modeling studies indicated that the most active compounds (8a and 8e), adopt a planar conformation, close to the shape of AMPPNP in the crystal structure of GSK-3. These compounds are stabilized by hydrophobic contacts between the 8-aromatic group and the protein adenine pocket and by electrostatic contacts. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.026
• 作为产物：
  描述：

  4,5-二氨基-6-氯嘧啶 、 2-萘甲酸 在 氯化铵 、 三氯氧磷 作用下， 反应 24.0h， 生成 6-chloro-8-(naphthalen-2-yl)-9H-purine
  参考文献：
  名称：

  Novel 8-arylated purines as inhibitors of glycogen synthase kinase

  摘要：

  A series of 8-arylated purine derivatives bearing either an aniline or an alkyl amide at position 6 were found to inhibit glycogen synthase kinase-3, with good selectivity over ten kinases. Molecular modeling studies indicated that the most active compounds (8a and 8e), adopt a planar conformation, close to the shape of AMPPNP in the crystal structure of GSK-3. These compounds are stabilized by hydrophobic contacts between the 8-aromatic group and the protein adenine pocket and by electrostatic contacts. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.026