5-amino-1-(2-hydroxyethyl)-3-phenyl-1H-pyrazole-4-carbonitrile | 1286278-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-1-(2-hydroxyethyl)-3-phenyl-1H-pyrazole-4-carbonitrile
• 英文别名: 5-Amino-1-(2-hydroxyethyl)-3-phenylpyrazole-4-carbonitrile；5-amino-1-(2-hydroxyethyl)-3-phenylpyrazole-4-carbonitrile
• CAS: 1286278-41-8
• 化学式: C₁₂H₁₂N₄O
• mdl: MFCD23264163
• 分子量: 228.253
• InChiKey: SVMBGRHDNDMIKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  87.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-1-(2-hydroxyethyl)-3-phenyl-1H-pyrazole-4-carbonitrile 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 1-(2-azidoethyl)-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine
  参考文献：
  名称：

  Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities

  摘要：

  A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB-361), and colon adenocarcinoma (HT-29). Hexyl triazolyl-substituted 3-phenylpyrazolopyrimidine exhibited inhibition of Src kinase with an IC50 value of 5.6 mu M. 4-Methoxyphenyl triazolyl-substituted 3-phenylpyrazolopyrimidine inhibited the cell proliferation of HT-29 and SK-Ov-3 by 73% and 58%, respectively, at a concentration of 50 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.047
• 作为产物：
  描述：

  α-cyano-β-hydroxycinnamonitrile 在 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-amino-1-(2-hydroxyethyl)-3-phenyl-1H-pyrazole-4-carbonitrile
  参考文献：
  名称：

  Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities

  摘要：

  A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB-361), and colon adenocarcinoma (HT-29). Hexyl triazolyl-substituted 3-phenylpyrazolopyrimidine exhibited inhibition of Src kinase with an IC50 value of 5.6 mu M. 4-Methoxyphenyl triazolyl-substituted 3-phenylpyrazolopyrimidine inhibited the cell proliferation of HT-29 and SK-Ov-3 by 73% and 58%, respectively, at a concentration of 50 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.047