1-(3-amino-4,5-bis(3,4,5-trimethoxyphenyl)-1H-pyrazol-1-yl)ethanone | 1152421-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3-amino-4,5-bis(3,4,5-trimethoxyphenyl)-1H-pyrazol-1-yl)ethanone
• 英文别名: 1-[3-Amino-4,5-bis(3,4,5-trimethoxyphenyl)pyrazol-1-yl]ethanone
• CAS: 1152421-29-8
• 化学式: C₂₃H₂₇N₃O₇
• 分子量: 457.483
• InChiKey: WIPRQEFBKBLOSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-oxo-2,3-bis(3,4,5-trimethoxyphenyl)propanenitrile 在 吡啶 、 盐酸 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 9.0h， 生成 1-(3-amino-4,5-bis(3,4,5-trimethoxyphenyl)-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  4,5‐Diaryl‐3‐aminopyrazole Derivatives as Analogs of Combretastatin A‐4: Synthesis and Biological Evaluation

  摘要：

  A series of cis‐restricted 4,5‐diaryl‐3‐aminopyrazole derivatives were synthesized and tested for their cytotoxic activity in vitro against five human cancer cell lines (K562, ECA‐109, A549, SMMC‐7721, and PC‐3). Compounds 5a, 5b, 5d, and 6b showed potent cytotoxicity against all tested cell lines. Primary mechanism research on compound 5a indicated that it was a potent inhibitor of tubulin polymerization, arresting cell cycle in G₂/M phase. The docking research showed the conformation of 5a overlaps well with CA‐4 in the crystallized protein complex, suggesting the 4,5‐diaryl‐3‐aminopyrazoles were good mimics of CA‐4.

  DOI：

  10.1002/ardp.201000069