6-(2-chlorophenyl)-N⁴-(2,6-dimethylphenyl)-pyrimidine-4,5-diamine | 939040-36-5

• 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: 6-(2-chlorophenyl)-N⁴-(2,6-dimethylphenyl)-pyrimidine-4,5-diamine
• 英文别名: 6-(2-chlorophenyl)-4-N-(2,6-dimethylphenyl)pyrimidine-4,5-diamine
• CAS: 939040-36-5
• 化学式: C₁₈H₁₇ClN₄
• 分子量: 324.813
• InChiKey: QPTJACDLBQWVML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2-chlorophenyl)-N⁴-(2,6-dimethylphenyl)-pyrimidine-4,5-diamine 、 N,N'-羰基二咪唑 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 2.5h， 以38%的产率得到6-(2-chlorophenyl)-9-(2,6-dimethylphenyl)-7H-purin-8-one
  参考文献：
  名称：

  Synthesis, Biological Testing, and Binding Mode Prediction of 6,9-Diarylpurin-8-ones as p38 MAP Kinase Inhibitors

  摘要：

  Based on the purine scaffold of ATP, derivatives of 6,9-diarylpurine-8-one were prepared and tested for their ability to inhibit p38 MAP kinase, a key enzyme in the cellular regulation of proinflammatory cytokines. The inhibitor design combines the purine system of the authentic cosubstrate ATP with various phenyl moieties to explore the selectivity for the two hydrophobic regions of the kinase's ATP-binding cleft. The present study indicates a new binding mode of our scaffold to p38 MAP kinase, which comprises the desired structural features of ATP and the N-phenyl-N-purin-6-yl ureas previously published by Wan et al. Combinations of Autodock and FlexX docking with different scoring functions were used to assess the postulated binding mode. The predictive power of different docking-scoring combinations was determined. The presented results may form a solid basis for further optimization cycles since our theoretical findings are consistent with our experimental binding data and supported by the literature.

  DOI：

  10.1021/jm061061w
• 作为产物：
  描述：

  4-chloro-6-(2-chlorophenyl)-5-nitro-pyrimidine 在 sulfided platinum on carbon 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 20.0 ℃ 、400.0 kPa 条件下， 反应 8.0h， 生成 6-(2-chlorophenyl)-N⁴-(2,6-dimethylphenyl)-pyrimidine-4,5-diamine
  参考文献：
  名称：

  Synthesis, Biological Testing, and Binding Mode Prediction of 6,9-Diarylpurin-8-ones as p38 MAP Kinase Inhibitors

  摘要：

  Based on the purine scaffold of ATP, derivatives of 6,9-diarylpurine-8-one were prepared and tested for their ability to inhibit p38 MAP kinase, a key enzyme in the cellular regulation of proinflammatory cytokines. The inhibitor design combines the purine system of the authentic cosubstrate ATP with various phenyl moieties to explore the selectivity for the two hydrophobic regions of the kinase's ATP-binding cleft. The present study indicates a new binding mode of our scaffold to p38 MAP kinase, which comprises the desired structural features of ATP and the N-phenyl-N-purin-6-yl ureas previously published by Wan et al. Combinations of Autodock and FlexX docking with different scoring functions were used to assess the postulated binding mode. The predictive power of different docking-scoring combinations was determined. The presented results may form a solid basis for further optimization cycles since our theoretical findings are consistent with our experimental binding data and supported by the literature.

  DOI：

  10.1021/jm061061w