2-(2-naphthyl)-1-(3,4,5-trimethoxyphenyl)-1H-imidazole

• 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-(2-naphthyl)-1-(3,4,5-trimethoxyphenyl)-1H-imidazole
• 英文别名: 2-(naphthalen-2-yl)-1-(3,5-trimethoxyphenyl)-1H-imidazole；2-naphthalen-2-yl-1-(3,4,5-trimethoxyphenyl)imidazole
• 化学式: C₂₂H₂₀N₂O₃
• 分子量: 360.412
• InChiKey: NJSASTDWMGNLHN-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 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2-naphthyl)-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

• Regiocontrolled Synthesis of 1,2-Diaryl-1H-imidazoles by Palladium- and Copper-Mediated Direct Coupling of 1-Aryl-1H-imidazoles with Aryl Halides under Ligandless Conditions
  作者：Fabio Bellina、Silvia Cauteruccio、Luisa Mannina、Renzo Rossi、Stéphane Viel

  DOI：10.1002/ejoc.200500636

  日期：2006.2

  involving the formation of an organocopper(I) derivatives followed by a transmetallation reaction with an arylpalladium(II) halide species and a reductive elimination, is proposed. New one-step procedures for the synthesis of 1,2,5-triaryl-1H-imidazoles, based on palladium- and copper-mediated arylation of 1-aryl-1H-imidazoles, have also been developed. Interestingly, some imidazole derivatives prepared in

  通过在 DMF 中将 1-芳基-1H-咪唑与芳基碘化物或溴化物直接偶联，以中等至高产率区域选择性地合成了多种 1,2-二芳基-1H-咪唑，包括选择性 COX-2 抑制剂。在无配体条件下存在 CsF 和催化量的 Pd(OAc)2。提出了这种新的高区域选择性 C-2 芳基化反应的可能机制，包括形成有机铜 (I) 衍生物，然后与芳基钯 (II) 卤化物物种进行金属转移反应和还原消除。还开发了基于钯和铜介导的 1-芳基-1H-咪唑芳基化的新一步法合成 1,2,5-三芳基-1H-咪唑。有趣的是，已发现本研究中制备的某些咪唑衍生物对某些人类肿瘤细胞系具有显着的细胞毒活性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)