2-(but-3-enyloxy)-5-iodo-1-methyl-1H-imidazole | 1051373-88-6

• 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-(but-3-enyloxy)-5-iodo-1-methyl-1H-imidazole
• 英文别名: 2-But-3-enoxy-5-iodo-1-methylimidazole
• CAS: 1051373-88-6
• 化学式: C₈H₁₁IN₂O
• 分子量: 278.093
• InChiKey: CNKRIXVBZGJVLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(but-3-enyloxy)-5-iodo-1-methyl-1H-imidazole 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 51.5h， 生成 4-methoxy-21-methyl-8,17-dioxa-19,21-diazatricyclo[16.2.1.0(2,7)]henicosa-1(20),2,4,6,18-pentaene
  参考文献：
  名称：

  New 5-Aryl-1H-imidazoles Display in Vitro Antitumor Activity against Apoptosis-Resistant Cancer Models, Including Melanomas, through Mitochondrial Targeting

  摘要：

  We designed and synthesized 48 aryl-1H-imidazole derivatives and investigated their in vitro growth inhibitory activity in cancer cell lines known to present various levels of resistance to proapoptotic stimuli. The IC50 in vitro growth inhibitory concentration of these compounds ranged from >100 mu M to single digit mu M. Among the most active compounds, 2i displayed similar in vitro growth inhibition in cancer cells independent of the cells' levels of resistance to proapoptotic stimuli and was found to be cytostatic in melanoma cell lines. Compound 2i was then tested by the National Cancer Institute Human Tumor Cell Line Anti-Cancer Drug Screen, and the NCI COMPARE algorithm did not reveal any correlation between its growth inhibition profiles with the NCI database compound profiles. The use of transcriptomically characterized melanoma models then enabled us to highlight mitochondrial targeting by 2i. This hypothesis was further confirmed by reactive oxygen production measurement and oxygen consumption analysis.

  DOI：

  10.1021/jm400287v
• 作为产物：
  描述：

  3-丁烯-1-醇 、 5-iodo-1-methyl-2-phenylsulfonyl-1H-imidazole 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以78%的产率得到2-(but-3-enyloxy)-5-iodo-1-methyl-1H-imidazole
  参考文献：
  名称：

  1,2,4-和1,2,5-三取代的咪唑的发散和区域​​选择性合成。

  摘要：

  已经开发了从容易获得的（两步）通用中间体中发散和区域​​选择性合成1,2,4-和1,2,5-三取代的咪唑的方法。该方法基于1-（N，N-二甲基氨磺酰基）-5-碘-2-苯基硫基-1H-咪唑的区域控制性N-烷基化（10）。当该中间体与三氟甲磺酸甲酯反应时，观察到选择性形成了相应的1,2,5-三取代的1H-咪唑。NMR研究表明，这种区域选择性可以通过将10原位快速异构化为其1,2,4-异构体（13），然后对其进行区域特异性N-烷基化来解决。相反，当将关键中间体10缓慢添加到Meerwein盐中时，异构化会受到限制，区域10的区域特异性N-烷基化会导致1,2,4-三取代的1H-咪唑具有高选择性。

  DOI：

  10.1021/jo801256b

文献信息

• Planar Chirality of Imidazole-Containing Macrocycles - Understanding and Tuning Atropisomerism
  作者：Emilie Van Den Berge、Jiří Pospíšil、Tran Trieu-Van、Laurent Collard、Raphaël Robiette

  DOI：10.1002/ejoc.201100805

  日期：2011.11

  The synthesis and characterization of imidazole-containing macrocycles displaying planar chirality has been achieved. HLPC and NMR studies revealed the crucial role of the alicyclic chain length in determining the rate of stereoisomerisation: 15- and 16-membered cyclic compounds are chiral whereas their larger-ringed analogues equilibrate rapidly at room temperature. Computational calculations are

  已经实现了显示平面手性的含咪唑大环的合成和表征。HLPC 和 NMR 研究揭示了脂环链长度在决定立体异构化速率方面的关键作用：15 和 16 元环状化合物是手性的，而它们的大环类似物在室温下迅速平衡。计算计算与实验观察结果非常一致，使我们能够了解两种阻转异构体之间的构象平衡所涉及的机制和相互作用。通过半制备手性 HPLC 分离 15 元大环的两种对映异构体使我们能够研究手性对其生物活性的影响。
• Synthesis and biological evaluation of novel imidazole-containing macrocycles
  作者：Prosper Nshimyumukiza、Emilie Van Den Berge、Bruno Delest、Tatjana Mijatovic、Robert Kiss、Jacqueline Marchand-Brynaert、Raphaël Robiette

  DOI：10.1016/j.tet.2010.04.070

  日期：2010.6

  A new family of compounds made of a 5-aryl-1H-imidazole motif included in a macrocycle has been designed and synthesized. The synthesis of the imidazole core makes use of our previously developed method for the regioselective preparation of 1,2,5-trisubstituted imidazoles while the construction of the macrocycle is based on a three steps sequence: SNAr, Suzuki coupling, and RCM reaction. Biological evaluation of synthesized imidazole-containing macrocycles revealed that they display actual binding activity toward A(3) adenosine (h) receptor, dopamine D-1 (h) receptor, chloride channel (GABA-gated), and choline transporter (h) CHT1. (C) 2010 Elsevier Ltd. All rights reserved.