methyl 5-(3-acetoxy-4-methoxyphenyl)-2,3-dihydro-4-(3,4,5-trimethoxyphenyl)-3-oxopyrazole-1-carboxylate | 1228170-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 5-(3-acetoxy-4-methoxyphenyl)-2,3-dihydro-4-(3,4,5-trimethoxyphenyl)-3-oxopyrazole-1-carboxylate
• 英文别名: methyl 3-(3-acetyloxy-4-methoxyphenyl)-5-oxo-4-(3,4,5-trimethoxyphenyl)-1H-pyrazole-2-carboxylate
• CAS: 1228170-03-3
• 化学式: C₂₃H₂₄N₂O₉
• 分子量: 472.452
• InChiKey: GJTNVKFFDDRGKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 5-(3-acetoxy-4-methoxyphenyl)-2,3-dihydro-4-(3,4,5-trimethoxyphenyl)-3-oxopyrazole-1-carboxylate 在 甲醇 、 sodium hydroxide 、 盐酸 、 水 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到5-(3-hydroxy-4-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,2-dihydro-3H-pyrazol-3-one
  参考文献：
  名称：

  Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies

  摘要：

  A series of pyrazolone-fused combretastatins and precursors were synthesized and their cytotoxicity as well as antitubulin potential was evaluated. The hydrazide 9f and the pyrazolone-fused combretastatins 12a, 12b and 12c were highly cytotoxic against various tumor cell lines including cisplatin resistant cells. The same compounds were also the best inhibitors of tubulin polymerization. Molecular modeling results showed that they bind the colchicine binding site at the tubulin heterodimer. The hydrazide 9f arrested HeLa cells in the G2/M phase of the cell cycle and strongly affected cell shape and microtubule network. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.006
• 作为产物：
  描述：

  以 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl 5-(3-acetoxy-4-methoxyphenyl)-2,3-dihydro-4-(3,4,5-trimethoxyphenyl)-3-oxopyrazole-1-carboxylate
  参考文献：
  名称：

  Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies

  摘要：

  A series of pyrazolone-fused combretastatins and precursors were synthesized and their cytotoxicity as well as antitubulin potential was evaluated. The hydrazide 9f and the pyrazolone-fused combretastatins 12a, 12b and 12c were highly cytotoxic against various tumor cell lines including cisplatin resistant cells. The same compounds were also the best inhibitors of tubulin polymerization. Molecular modeling results showed that they bind the colchicine binding site at the tubulin heterodimer. The hydrazide 9f arrested HeLa cells in the G2/M phase of the cell cycle and strongly affected cell shape and microtubule network. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.006