6-(3,4-difluorophenyl)-9-(tetrahydropyran-2-yl)-2-[(tetrahydropyran-2-yl)amino]purine

• 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-(3,4-difluorophenyl)-9-(tetrahydropyran-2-yl)-2-[(tetrahydropyran-2-yl)amino]purine
• 英文别名: 6-(3,4-difluorophenyl)-N,9-bis(oxan-2-yl)purin-2-amine
• 化学式: C₂₁H₂₃F₂N₅O₂
• 分子量: 415.443
• InChiKey: AAARBTRVRVZHQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  74.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-(3,4-difluorophenyl)-9-(tetrahydropyran-2-yl)-2-[(tetrahydropyran-2-yl)amino]purine 在 Dowex 50*8 (H⁺) 作用下， 以 甲醇 、 水 为溶剂， 以80%的产率得到2-amino-6-(3,4-difluorophenyl)purine
  参考文献：
  名称：

  Synthesis and Cytostatic Activity of Substituted 6-Phenylpurine Bases and Nucleosides:  Application of the Suzuki−Miyaura Cross-Coupling Reactions of 6-Chloropurine Derivatives with Phenylboronic Acids

  摘要：

  The Suzuki-Miyaura reaction of protected 6-chloropurine and 2-amino-6-chloropurine bases and nucleosides with substituted phenylboronic acids led to the corresponding protected 6-(substituted phenyl)purine derivatives 6-9. Their deprotection yielded a series of substituted 6-phenylpurine bases and nucleosides 10-13. Significant cytostatic activity (IC50 0.25-20 mu mol/L) in CCRF-CEM, HeLa, and L1210 cell lines was found for several 6-(4-X-substituted phenyl)purine ribonucleosides 12 (X = H, F, Cl, and OR), while the 6-phenylpurine and 2-amino-6-phenylpurine bases 10 and 11, as well as 2-amino-6-phenylpurine ribosides 13, were entirely inactive against these cell lines.

  DOI：

  10.1021/jm991167+
• 作为产物：
  描述：

  3,4-二氟苯硼酸 、 6-chloro-2-(tetrahydropyran-2-yl)amino-9-(tetrahydropyran-2-yl)purine 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以60%的产率得到6-(3,4-difluorophenyl)-9-(tetrahydropyran-2-yl)-2-[(tetrahydropyran-2-yl)amino]purine
  参考文献：
  名称：

  Synthesis and Cytostatic Activity of Substituted 6-Phenylpurine Bases and Nucleosides:  Application of the Suzuki−Miyaura Cross-Coupling Reactions of 6-Chloropurine Derivatives with Phenylboronic Acids

  摘要：

  The Suzuki-Miyaura reaction of protected 6-chloropurine and 2-amino-6-chloropurine bases and nucleosides with substituted phenylboronic acids led to the corresponding protected 6-(substituted phenyl)purine derivatives 6-9. Their deprotection yielded a series of substituted 6-phenylpurine bases and nucleosides 10-13. Significant cytostatic activity (IC50 0.25-20 mu mol/L) in CCRF-CEM, HeLa, and L1210 cell lines was found for several 6-(4-X-substituted phenyl)purine ribonucleosides 12 (X = H, F, Cl, and OR), while the 6-phenylpurine and 2-amino-6-phenylpurine bases 10 and 11, as well as 2-amino-6-phenylpurine ribosides 13, were entirely inactive against these cell lines.

  DOI：

  10.1021/jm991167+

文献信息

• Synthesis and Cytostatic Activity of Substituted 6-Phenylpurine Bases and Nucleosides:  Application of the Suzuki−Miyaura Cross-Coupling Reactions of 6-Chloropurine Derivatives with Phenylboronic Acids
  作者：Michal Hocek、Antonín Holý、Ivan Votruba、Hana Dvořáková

  DOI：10.1021/jm991167+

  日期：2000.5.1

  The Suzuki-Miyaura reaction of protected 6-chloropurine and 2-amino-6-chloropurine bases and nucleosides with substituted phenylboronic acids led to the corresponding protected 6-(substituted phenyl)purine derivatives 6-9. Their deprotection yielded a series of substituted 6-phenylpurine bases and nucleosides 10-13. Significant cytostatic activity (IC50 0.25-20 mu mol/L) in CCRF-CEM, HeLa, and L1210 cell lines was found for several 6-(4-X-substituted phenyl)purine ribonucleosides 12 (X = H, F, Cl, and OR), while the 6-phenylpurine and 2-amino-6-phenylpurine bases 10 and 11, as well as 2-amino-6-phenylpurine ribosides 13, were entirely inactive against these cell lines.