1-[(4-nitrophenyl)sulfonyl]-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-amine | 1376687-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[(4-nitrophenyl)sulfonyl]-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-amine
• 英文别名: 1-[(4-Nitrophenyl)sulfonyl]-3-phenyl-1h-pyrazolo[3,4-d]pyrimidine-4-amine；1-(4-nitrophenyl)sulfonyl-3-phenylpyrazolo[3,4-d]pyrimidin-4-amine
• CAS: 1376687-97-6
• 化学式: C₁₇H₁₂N₆O₄S
• 分子量: 396.386
• InChiKey: BXFJXRRNLGMFRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-氨基-5-苯基-1H-吡唑-4-甲腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 1-[(4-nitrophenyl)sulfonyl]-3-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-amine
  参考文献：
  名称：

  Pyrazolo[3,4-d]pyrimidine analogues: synthesis, characterization and their in vitro antiamoebic activity

  摘要：

  Pyrazolo[3,4-d]pyrimidine analogues were synthesized by treating 3-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-amine with different sulfonyl chlorides and triethylamine in dry dichloromethane. The structure of all the compounds was elucidated by spectral data and their purity was confirmed by elemental analysis. In vitro antiamoebic activity was performed against HM1:IMSS strain of Entamoeba histolytica and two compounds, 4 (IC50 = 0.57) and 6 (IC50 = 0.68), were found better inhibitors than the reference drug metronidazole (IC50 = 1.80). Further, both the compounds (4 and 6) were low cytotoxic against the human breast cancer MCF-7 cell line in the concentration range of 2.5-250 mu M. These preliminary results reveal that pyrazolo[3,4-d]pyrimidine analogues could help in designing better molecules with enhanced antiamoebic activity.

  DOI：

  10.1007/s00044-012-0070-6

文献信息

• Pyrazolo[3,4-d]pyrimidine analogues: synthesis, characterization and their in vitro antiamoebic activity
  作者：Shadab Miyan Siddiqui、Attar Salahuddin、Amir Azam

  DOI：10.1007/s00044-012-0070-6

  日期：2013.2

  Pyrazolo[3,4-d]pyrimidine analogues were synthesized by treating 3-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4-amine with different sulfonyl chlorides and triethylamine in dry dichloromethane. The structure of all the compounds was elucidated by spectral data and their purity was confirmed by elemental analysis. In vitro antiamoebic activity was performed against HM1:IMSS strain of Entamoeba histolytica and two compounds, 4 (IC50 = 0.57) and 6 (IC50 = 0.68), were found better inhibitors than the reference drug metronidazole (IC50 = 1.80). Further, both the compounds (4 and 6) were low cytotoxic against the human breast cancer MCF-7 cell line in the concentration range of 2.5-250 mu M. These preliminary results reveal that pyrazolo[3,4-d]pyrimidine analogues could help in designing better molecules with enhanced antiamoebic activity.