5-(naphthalen-2-yl)-1-(3,4,5-trimethoxyphenyl)-1H-imidazole | 915954-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(naphthalen-2-yl)-1-(3,4,5-trimethoxyphenyl)-1H-imidazole
• 英文别名: 5-naphthalen-2-yl-1-(3,4,5-trimethoxyphenyl)imidazole
• CAS: 915954-53-9
• 化学式: C₂₂H₂₀N₂O₃
• 分子量: 360.412
• InChiKey: VQIFHAGEERVOKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-碘萘 、 1-(3,4,5-trimethoxyphenyl)-1H-imidazole 在 palladium diacetate 三苯胂 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-(naphthalen-2-yl)-1-(3,4,5-trimethoxyphenyl)-1H-imidazole
  参考文献：
  名称：

  Novel imidazole-based combretastatin A-4 analogues: Evaluation of their in vitro antitumor activity and molecular modeling study of their binding to the colchicine site of tubulin

  摘要：

  The in vitro antitumor activity of novel combretastatin-like 1,5- and 1,2-diaryl-1H-imidazoles was evaluated against the NCI 60 human tumor cell lines panel. Compounds 2d and 2g proved to be more cytotoxic than CA-4 in tests involving their evaluation over a 10(-4)-10(-8) range. Docking experiments showed a good correlation between the MG_MID Log GI(50) values of all these compounds and their calculated interaction energies with the colchicine binding site of alpha beta-tubulin. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.087

文献信息

• Vascular Disrupting Activity of Tubulin-Binding 1,5-Diaryl-1<i>H</i>-imidazoles
  作者：Katiuscia Bonezzi、Giulia Taraboletti、Patrizia Borsotti、Fabio Bellina、Renzo Rossi、Raffaella Giavazzi

  DOI：10.1021/jm900968s

  日期：2009.12.10

  Highly cytotoxic 1,5-diaryl-1H-imidazoles were studied to clarify the relationship between cytotoxicity and activity as vascular disrupting agents (VDA). All the compounds disorganized the tubulin cytoskeleton, affected endothelial cell morphology and capillary formation in vitro, and caused vessel shutdown and tumor necrosis in vivo, thus confirming their vascular disrupting properties. Nonetheless, the substitution patterns oil the imidazole ring, responsible for greater interaction energy with tubulin and higher cytotoxicity, were not associated to greater vascular disrupting activity.
• Novel imidazole-based combretastatin A-4 analogues: Evaluation of their in vitro antitumor activity and molecular modeling study of their binding to the colchicine site of tubulin
  作者：Fabio Bellina、Silvia Cauteruccio、Susanna Monti、Renzo Rossi

  DOI：10.1016/j.bmcl.2006.08.087

  日期：2006.11

  The in vitro antitumor activity of novel combretastatin-like 1,5- and 1,2-diaryl-1H-imidazoles was evaluated against the NCI 60 human tumor cell lines panel. Compounds 2d and 2g proved to be more cytotoxic than CA-4 in tests involving their evaluation over a 10(-4)-10(-8) range. Docking experiments showed a good correlation between the MG_MID Log GI(50) values of all these compounds and their calculated interaction energies with the colchicine binding site of alpha beta-tubulin. (c) 2006 Elsevier Ltd. All rights reserved.