4-chloro-2-[(2-chloro-9-cyclopentyl-9H-purin-6-ylamino)methyl]phenol | 1448338-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 4-chloro-2-[(2-chloro-9-cyclopentyl-9H-purin-6-ylamino)methyl]phenol
• 英文别名: 4-Chloro-2-[[(2-chloro-9-cyclopentylpurin-6-yl)amino]methyl]phenol；4-chloro-2-[[(2-chloro-9-cyclopentylpurin-6-yl)amino]methyl]phenol
• CAS: 1448338-28-0
• 化学式: C₁₇H₁₇Cl₂N₅O
• 分子量: 378.261
• InChiKey: ZKFSGIJWZODCNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  75.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,6-二氯嘌呤 在 偶氮二异丁腈 、 偶氮二甲酸二异丙酯 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 丙醇 为溶剂， 反应 6.0h， 生成 4-chloro-2-[(2-chloro-9-cyclopentyl-9H-purin-6-ylamino)methyl]phenol
  参考文献：
  名称：

  A Novel Series of Highly Potent 2,6,9-Trisubstituted Purine Cyclin-Dependent Kinase Inhibitors

  摘要：

  The inhibition of overactive CDKs during cancer remains an important strategy in cancer drug development. We synthesized and screened a novel series of 2-substituted-6-biarylmethylamino-9-cyclopentylpurine derivatives for improved CDK inhibitory activity and antiproliferative effects. One of the most potent compounds, 6b, exhibited strong cytotoxicity in the human melanoma cell line G361 that correlated with robust CDK1 and CDK2 inhibition and caspase activation. In silico modeling of 6b in the active site of CDK2 revealed a high interaction energy, which we believe is due to the 6-heterobiarylmethylamino substitution of the purine moiety.

  DOI：

  10.1021/jm4006884