6-chloro-2-methyl-9-[3-(N,N-dimethylamino)phenyl]purin-8-one | 1362239-42-6

• 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-chloro-2-methyl-9-[3-(N,N-dimethylamino)phenyl]purin-8-one
• 英文别名: 6-chloro-9-[3-(dimethylamino)phenyl]-2-methyl-7H-purin-8-one
• CAS: 1362239-42-6
• 化学式: C₁₄H₁₄ClN₅O
• 分子量: 303.751
• InChiKey: VUXIDCQMUGKEDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-2-methyl-9-[3-(N,N-dimethylamino)phenyl]purin-8-one 、 氯甲酸苯酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到6-chloro-9-(3-(N,N-dimethylamino)phenyl)-2-methyl-9H-purin-8-yl phenyl carbonate
  参考文献：
  名称：

  Efficient synthesis and anti-enteroviral activity of 9-arylpurines

  摘要：

  To further explore the anti-enteroviral activity of 9-aryl-6-chloropurines, three different series of compounds with a dialkylamino, (alkyl)amido, or oxazolidinone substituent at the aryl ring have been synthesized, in most cases with the aid of microwave-assisted synthesis. The resulting compounds efficiently inhibit Coxsackie virus type B3 (CVB3) replication with EC50 values varying from 3 to 15 mu M, and with no significant toxicity in Vero cells. The most potent compounds also selectively inhibit the replication of other enteroviruses including Coxsackie virus B4 and Echo virus 11. The cross-resistance studies performed with different 9-aryl-6-chloropurines indicate that they all belong to the same pharmacological family and differ from other CVB3 drugs such as enviroxime. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.022
• 作为产物：
  描述：

  2-甲基-4,6-二氯-5-氨基嘧啶 在 盐酸 、 乙酸酐 作用下， 以 四氢呋喃 、 异丁醇 、 水 为溶剂， 反应 0.5h， 生成 6-chloro-2-methyl-9-[3-(N,N-dimethylamino)phenyl]purin-8-one
  参考文献：
  名称：

  Efficient synthesis and anti-enteroviral activity of 9-arylpurines

  摘要：

  To further explore the anti-enteroviral activity of 9-aryl-6-chloropurines, three different series of compounds with a dialkylamino, (alkyl)amido, or oxazolidinone substituent at the aryl ring have been synthesized, in most cases with the aid of microwave-assisted synthesis. The resulting compounds efficiently inhibit Coxsackie virus type B3 (CVB3) replication with EC50 values varying from 3 to 15 mu M, and with no significant toxicity in Vero cells. The most potent compounds also selectively inhibit the replication of other enteroviruses including Coxsackie virus B4 and Echo virus 11. The cross-resistance studies performed with different 9-aryl-6-chloropurines indicate that they all belong to the same pharmacological family and differ from other CVB3 drugs such as enviroxime. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.022