2-oxo-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1H-imidazole-4-carboxylic acid | 1204430-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-oxo-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1H-imidazole-4-carboxylic acid
• 英文别名: 2-Oxo-5-(3,4,5-trimethoxyphenyl)-1,3-dihydroimidazole-4-carboxylic acid
• CAS: 1204430-82-9
• 化学式: C₁₃H₁₄N₂O₆
• 分子量: 294.264
• InChiKey: PAGHGYKPDDFBTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-oxo-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1H-imidazole-4-carboxylic acid 在 盐酸 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 tin(ll) chloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 N-(3-amino-4-methoxyphenyl)-2-oxo-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1H-imidazole-4-carboxamide
  参考文献：
  名称：

  Imidazolone–amide bridges and their effects on tubulin polymerization in cis-locked vinylogous combretastatin-A4 analogues: Synthesis and biological evaluation

  摘要：

  A series of novel combretastatin-A4 analogues in which the cis-olefinic bridge is replaced by an imidazolone-amide were synthesized, and their cytotoxicity and tubulin-polymerization inhibitory activities were evaluated. These compounds appear to be potential tubulin-polymerization inhibitors. Compounds 10, 9b and 9c, bearing 3'-NH2-4'-OCH3, 4'-CH3 and 3'-CH3-substituted 1-phenyl B-ring, confer optimal bioactivity. The binding modes of these compounds to tubulin were obtained by molecular docking, which can explain the compounds' structure-activity relationship. The studies presented here provide a new structural type for the development of novel antitumor agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.068
• 作为产物：
  描述：

  ethyl 2-bromo-3-oxo-3-(3,4,5-trimethoxyphenyl)propanoate 在 三乙胺 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-oxo-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1H-imidazole-4-carboxylic acid
  参考文献：
  名称：

  Imidazolone–amide bridges and their effects on tubulin polymerization in cis-locked vinylogous combretastatin-A4 analogues: Synthesis and biological evaluation

  摘要：

  A series of novel combretastatin-A4 analogues in which the cis-olefinic bridge is replaced by an imidazolone-amide were synthesized, and their cytotoxicity and tubulin-polymerization inhibitory activities were evaluated. These compounds appear to be potential tubulin-polymerization inhibitors. Compounds 10, 9b and 9c, bearing 3'-NH2-4'-OCH3, 4'-CH3 and 3'-CH3-substituted 1-phenyl B-ring, confer optimal bioactivity. The binding modes of these compounds to tubulin were obtained by molecular docking, which can explain the compounds' structure-activity relationship. The studies presented here provide a new structural type for the development of novel antitumor agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.068