2-(2-chlorophenyl)-benzo[b]thiophene-3-carboxaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(2-chlorophenyl)-benzo[b]thiophene-3-carboxaldehyde
• 英文别名: 2-(2-Chlorophenyl)-1-benzothiophene-3-carbaldehyde
• 化学式: C₁₅H₉ClOS
• 分子量: 272.755
• InChiKey: ZAHJNVOWZDZMQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲醛苯并噻吩 、 2-溴氯苯 在 palladium diacetate 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以59%的产率得到2-(2-chlorophenyl)-benzo[b]thiophene-3-carboxaldehyde
  参考文献：
  名称：

  Synthesis and evaluation of new arylbenzo[b]thiophene and diarylthiophene derivatives as inhibitors of the NorA multidrug transporter of Staphylococcus aureus

  摘要：

  The synthesis based on palladium catalytic coupling of 38 new-arylated benzo[b]thiophenes or thiophenes is described in a few steps. We also report the direct arylation of the position 3 of the benzo[b]thiophenic structure, a 'one pot' 2,5-heterodiarylation of thiophenes as well as the synthesis of precursors of amino-acids with a 2-arylated benzo[b]thiophene core. These compounds were evaluated on bacteria strains: most of them did not exhibit any antibiotic activity but were found to selectively inhibit the NorA multidrug transporter of Staphylococcus aureus. As such, they restored the activity of the NorA substrates ciprofloxacin against a resistant S. aureus strain in which this efflux pump is over-expressed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.023

文献信息

• Synthesis and evaluation of new arylbenzo[b]thiophene and diarylthiophene derivatives as inhibitors of the NorA multidrug transporter of Staphylococcus aureus
  作者：Jérémie Fournier dit Chabert、Béatrice Marquez、Luc Neville、Lionel Joucla、Sylvie Broussous、Pascale Bouhours、Emilie David、Stéphane Pellet-Rostaing、Bernard Marquet、Nicole Moreau、Marc Lemaire

  DOI：10.1016/j.bmc.2007.04.023

  日期：2007.7

  The synthesis based on palladium catalytic coupling of 38 new-arylated benzo[b]thiophenes or thiophenes is described in a few steps. We also report the direct arylation of the position 3 of the benzo[b]thiophenic structure, a 'one pot' 2,5-heterodiarylation of thiophenes as well as the synthesis of precursors of amino-acids with a 2-arylated benzo[b]thiophene core. These compounds were evaluated on bacteria strains: most of them did not exhibit any antibiotic activity but were found to selectively inhibit the NorA multidrug transporter of Staphylococcus aureus. As such, they restored the activity of the NorA substrates ciprofloxacin against a resistant S. aureus strain in which this efflux pump is over-expressed. (c) 2007 Elsevier Ltd. All rights reserved.