2-(Benzenesulfonyl)-5-(2-hex-5-enoxyphenyl)-1-methylimidazole | 1448857-92-8

• 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-(Benzenesulfonyl)-5-(2-hex-5-enoxyphenyl)-1-methylimidazole
• 英文别名: 2-(benzenesulfonyl)-5-(2-hex-5-enoxyphenyl)-1-methylimidazole
• CAS: 1448857-92-8
• 化学式: C₂₂H₂₄N₂O₃S
• 分子量: 396.51
• InChiKey: DKDHTSRRZSXYPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-hexenyl methanesulfonate 在 四(三苯基膦)钯 、 正丁基锂 、 四丁基碘化铵 、 sodium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(Benzenesulfonyl)-5-(2-hex-5-enoxyphenyl)-1-methylimidazole
  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

文献信息

• 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.
• New 5-Aryl-1<i>H</i>-imidazoles Display in Vitro Antitumor Activity against Apoptosis-Resistant Cancer Models, Including Melanomas, through Mitochondrial Targeting
  作者：Véronique Mathieu、Emilie Van Den Berge、Justine Ceusters、Tomasz Konopka、Antonin Cops、Céline Bruyère、Christine Pirker、Walter Berger、Tran Trieu-Van、Didier Serteyn、Robert Kiss、Raphaël Robiette

  DOI：10.1021/jm400287v

  日期：2013.9.12

  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.