6-chloro-2,8,9-trimethyl-9H-purine

• 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: 6-chloro-2,8,9-trimethyl-9H-purine
• 英文别名: 6-Chloro-2,8,9-trimethylpurine
• 化学式: C₈H₉ClN₄
• 分子量: 196.639
• InChiKey: RQWKLXXJMZLPBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-2,8,9-trimethyl-9H-purine 在 盐酸 、 caesium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 2.67h， 生成 N-ethyl-N-(4-methoxyphenyl)-2,8,9-trimethyl-9H-purin-6-amine
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 6-phenylaminopurines

  摘要：

  A series of novel 6-phenylaminopurines have been efficiently synthesized in 3 steps exploring different groups at positions 2, 8 and 9 of the purine ring and at the exocyclic nitrogen atom at position 6. Among the newly described purines, five compounds showed antiproliferative activity with IC50 values below 10 mu M, the tetrahydroquinoline derivative at position 6 of phenylaminopurine being the most active of the series in the six cell lines tested. Moreover, the compounds induced G(2)/M phase arrest in human cervical carcinoma HeLa cells as reported for tubulin depolymerizing agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.093
• 作为产物：
  描述：

  2-甲基-4,6-二氯-5-氨基嘧啶 在 乙基磺酸 作用下， 以 1,4-二氧六环 、 水 、 乙酸酐 为溶剂， 反应 0.25h， 生成 6-chloro-2,8,9-trimethyl-9H-purine
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 6-phenylaminopurines

  摘要：

  A series of novel 6-phenylaminopurines have been efficiently synthesized in 3 steps exploring different groups at positions 2, 8 and 9 of the purine ring and at the exocyclic nitrogen atom at position 6. Among the newly described purines, five compounds showed antiproliferative activity with IC50 values below 10 mu M, the tetrahydroquinoline derivative at position 6 of phenylaminopurine being the most active of the series in the six cell lines tested. Moreover, the compounds induced G(2)/M phase arrest in human cervical carcinoma HeLa cells as reported for tubulin depolymerizing agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.093

文献信息

• Synthesis and antiproliferative activity of 6-phenylaminopurines
  作者：María-Dolores Canela、Sandra Liekens、María-José Camarasa、Eva María Priego、María-Jesús Pérez-Pérez

  DOI：10.1016/j.ejmech.2014.09.093

  日期：2014.11

  A series of novel 6-phenylaminopurines have been efficiently synthesized in 3 steps exploring different groups at positions 2, 8 and 9 of the purine ring and at the exocyclic nitrogen atom at position 6. Among the newly described purines, five compounds showed antiproliferative activity with IC50 values below 10 mu M, the tetrahydroquinoline derivative at position 6 of phenylaminopurine being the most active of the series in the six cell lines tested. Moreover, the compounds induced G(2)/M phase arrest in human cervical carcinoma HeLa cells as reported for tubulin depolymerizing agents. (C) 2014 Elsevier Masson SAS. All rights reserved.