2-bromo-1-(hex-5-en-1-yloxy)-4-methoxybenzene | 1236074-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-bromo-1-(hex-5-en-1-yloxy)-4-methoxybenzene
• CAS: 1236074-07-9
• 化学式: C₁₃H₁₇BrO₂
• 分子量: 285.181
• InChiKey: NAIWMIUFMAKJBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(hex-5-en-1-yloxy)-4-methoxybenzene 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 、 水 为溶剂， 反应 1.0h， 生成 2-(but-3-en-yloxy)-5-[2-(hex-5-en-1-yloxy)-5-methoxyphenyl]-1-methyl-1H-imidazole
  参考文献：
  名称：

  Synthesis and biological evaluation of novel imidazole-containing macrocycles

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.04.070
• 作为产物：
  描述：

  5-己烯-1-醇 在 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 2-bromo-1-(hex-5-en-1-yloxy)-4-methoxybenzene
  参考文献：
  名称：

  Synthesis and biological evaluation of novel imidazole-containing macrocycles

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.04.070

文献信息

• 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.