6-benzylsulfanyl-8-(4-chlorophenyl)-7-methyl-7H-purine | 1092101-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-benzylsulfanyl-8-(4-chlorophenyl)-7-methyl-7H-purine
• 英文别名: 6-Benzylsulfanyl-8-(4-chlorophenyl)-7-methylpurine
• CAS: 1092101-22-8
• 化学式: C₁₉H₁₅ClN₄S
• 分子量: 366.874
• InChiKey: SWXKRHZDEWHEAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-benzylsulfanyl-8-(4-chlorophenyl)-7-methyl-7H-purine 在 间氯过氧苯甲酸 、 calcium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 6-Benzylsulfonyl-8-(4-chlorophenyl)-7-methylpurine
  参考文献：
  名称：

  Synthesis of 6,7,8-Trisubstituted Purines via a Copper-Catalyzed Amidation Reaction

  摘要：

  We report herein an efficient method for the synthesis of 6,7,8-trisubstituted purines via a copper-catalyzed amidation reaction from easily accessible starting materials. Furthermore, the resulting 6-benzylsulfanyl-substituted purine derivatives may be readily oxidized for substitution by nucleophiles to give access to 6,7,8- trisubstituted purines for biological screening purposes.

  DOI：

  10.1021/jo802248g
• 作为产物：
  描述：

  (4-benzylsulfanyl-6-iodo-pyrimidin-5-yl)-methyl-amine 、 4-氯苯甲酰胺 在 copper(l) iodide 、 caesium carbonate 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 以75%的产率得到6-benzylsulfanyl-8-(4-chlorophenyl)-7-methyl-7H-purine
  参考文献：
  名称：

  Synthesis of 6,7,8-Trisubstituted Purines via a Copper-Catalyzed Amidation Reaction

  摘要：

  We report herein an efficient method for the synthesis of 6,7,8-trisubstituted purines via a copper-catalyzed amidation reaction from easily accessible starting materials. Furthermore, the resulting 6-benzylsulfanyl-substituted purine derivatives may be readily oxidized for substitution by nucleophiles to give access to 6,7,8- trisubstituted purines for biological screening purposes.

  DOI：

  10.1021/jo802248g

文献信息

• Novel 8-arylated purines as inhibitors of glycogen synthase kinase
  作者：Nada Ibrahim、Liliane Mouawad、Michel Legraverend

  DOI：10.1016/j.ejmech.2010.04.026

  日期：2010.8

  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.