5-amino-4-chloro-6-(4-dimethylaminophenyl)pyrimidine | 850791-74-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-amino-4-chloro-6-(4-dimethylaminophenyl)pyrimidine
• 英文别名: 6-chloro-N4-(4-di-methylaminobenzyl)-pyrimidine-4,5-diamine；6-chloro-4-N-[[4-(dimethylamino)phenyl]methyl]pyrimidine-4,5-diamine
• CAS: 850791-74-1
• 化学式: C₁₃H₁₆ClN₅
• 分子量: 277.757
• InChiKey: AQISMSUUPKCDTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-amino-4-chloro-6-(4-dimethylaminophenyl)pyrimidine 在 bis(triphenylphosphine)palladium(II)-chloride 、 乙基磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 9-(4-Dimethylaminophenylmethyl)-6-(2-furyl)-9H-purine
  参考文献：
  名称：

  Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines

  摘要：

  9-Aryl-, 9-arylsulfonyl- and 9-benzyl-6-(2-furyl)purines were synthesized by N-alkylation or N-arylation of the purine followed by Stille coupling to introduce the faryl substituent in the 6-position and the compounds screened for activity against Mycobacterium tuberculosis. The 9-aryl- and 9-sulfonylarylpurines exhibited weak activity toward the bacteria, but 9-benzylpurines were good inhibitors especially those carrying electron-donating substituents on the phenyl ring. A chlorine atom in the purine 2-position further enhanced activity. The high antimycobacterial activity (MIC 0.39,mu g/mL against M. tuberculosis), low toxicity against mammalian cells and activity inside macrophages found for 2-chloro-6-(2-furyl)-9-(4-methoxyphenylmethyl)9H-purine makes this compound a highly interesting potential antituberculosis drug.

  DOI：

  10.1021/jm0408924
• 作为产物：
  描述：

  4,6-二氯-5-氨基嘧啶 、 4-(dimethylamino)benzylamine dihydrochloride salt 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 22.08h， 以57%的产率得到5-amino-4-chloro-6-(4-dimethylaminophenyl)pyrimidine
  参考文献：
  名称：

  Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-furyl)purines

  摘要：

  9-Aryl-, 9-arylsulfonyl- and 9-benzyl-6-(2-furyl)purines were synthesized by N-alkylation or N-arylation of the purine followed by Stille coupling to introduce the faryl substituent in the 6-position and the compounds screened for activity against Mycobacterium tuberculosis. The 9-aryl- and 9-sulfonylarylpurines exhibited weak activity toward the bacteria, but 9-benzylpurines were good inhibitors especially those carrying electron-donating substituents on the phenyl ring. A chlorine atom in the purine 2-position further enhanced activity. The high antimycobacterial activity (MIC 0.39,mu g/mL against M. tuberculosis), low toxicity against mammalian cells and activity inside macrophages found for 2-chloro-6-(2-furyl)-9-(4-methoxyphenylmethyl)9H-purine makes this compound a highly interesting potential antituberculosis drug.

  DOI：

  10.1021/jm0408924

文献信息

• Purine compounds
  申请人：Gundersen Lise-Lotte

  公开号：US20070203159A1

  公开（公告）日：2007-08-30

  The invention provides an antimycobacterial 6-aryl-9-(m- or p-substituted-benzyl) purine and purine analog compounds.

  这项发明提供了一种抗分枝杆菌的6-芳基-9-(m-或p-取代苄基)嘌呤和嘌呤类似化合物。