1-(2-cyano-ethyl)-1H-pyrazole-3-carboxylic acid | 1338812-47-7

• 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-(2-cyano-ethyl)-1H-pyrazole-3-carboxylic acid
• 英文别名: 1-(2-Cyanoethyl)pyrazole-3-carboxylic acid；1-(2-cyanoethyl)pyrazole-3-carboxylic acid
• CAS: 1338812-47-7
• 化学式: C₇H₇N₃O₂
• 分子量: 165.151
• InChiKey: NWTWTXLUBHHGKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-4-(trans-3-amino-2,2,4,4-tetramethylcyclobutoxy)benzonitrile 、 1-(2-cyano-ethyl)-1H-pyrazole-3-carboxylic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 N-[trans-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]-1-(2-cyanoethyl)-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Discovery of Aryloxy Tetramethylcyclobutanes as Novel Androgen Receptor Antagonists

  摘要：

  An aryloxy tetramethylcyclobutane was identified as a novel template for androgen receptor (AR) antagonists via cell-based high-throughput screening. Follow-up to the initial "hit" established 5 as a viable lead. Further optimization to achieve full AR antagonism led to the discovery of 26 and 30, both of which demonstrated excellent in vivo tumor growth inhibition upon oral administration in a castration-resistant prostate cancer (CRPC) animal model.

  DOI：

  10.1021/jm201059s
• 作为产物：
  描述：

  1-(2-cyano-ethyl)-1H-pyrazole-3-carboxylic acid methyl ester 在 lithium hydroxide monohydrate 作用下， 以 甲醇 为溶剂， 反应 26.0h， 以67%的产率得到1-(2-cyano-ethyl)-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  Discovery of Aryloxy Tetramethylcyclobutanes as Novel Androgen Receptor Antagonists

  摘要：

  An aryloxy tetramethylcyclobutane was identified as a novel template for androgen receptor (AR) antagonists via cell-based high-throughput screening. Follow-up to the initial "hit" established 5 as a viable lead. Further optimization to achieve full AR antagonism led to the discovery of 26 and 30, both of which demonstrated excellent in vivo tumor growth inhibition upon oral administration in a castration-resistant prostate cancer (CRPC) animal model.

  DOI：

  10.1021/jm201059s