4-Methoxy-2-(5-nitro-1H-indol-2-yl)benzoic acid | 874752-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-Methoxy-2-(5-nitro-1H-indol-2-yl)benzoic acid
• 英文别名: 4-methoxy-2-(5-nitro-1H-indol-2-yl)benzoic acid
• CAS: 874752-03-1
• 化学式: C₁₆H₁₂N₂O₅
• 分子量: 312.282
• InChiKey: DPAXCOMMXJRBBO-UHFFFAOYSA-N

物化性质

• 熔点：
  206-208 °C
• 沸点：
  555.2±45.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Methoxy-2-(5-nitro-1H-indol-2-yl)benzoic acid 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到[4-methoxy-2-(5-nitro-1H-indol-2-yl)phenyl]methanol
  参考文献：
  名称：

  Synthesis of functionalised 2-aryl-5-nitro-1H-indoles and their activity as bacterial NorA efflux pump inhibitors

  摘要：

  In order to develop structure-activity relationships and to provide access to antibacterial agents for dual action studies, a variety of aryl group-substituted 2-aryl-5-nitro-1H-indoles were synthesized and the activity of the compounds assessed as inhibitors of the NorA multidrug resistance pump in the bacterium Staphylococcus aureus. The NorA protein from the major facilitator superfamily of efflux pumps confers resistance to a variety of structurally dissimilar antimicrobials such as norfloxacin, ethidium bromide, berberine and acrillavin. The compound [4-benzyloxy-2-(5-nitro-1H-2-yl)-phenyl]-methanol was the most potent pump inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.019
• 作为产物：
  描述：

  5-硝基吲哚 在 palladium diacetate 4-二甲氨基吡啶 、 potassium tert-butylate 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 28.0h， 生成 4-Methoxy-2-(5-nitro-1H-indol-2-yl)benzoic acid
  参考文献：
  名称：

  Synthesis of functionalised 2-aryl-5-nitro-1H-indoles and their activity as bacterial NorA efflux pump inhibitors

  摘要：

  In order to develop structure-activity relationships and to provide access to antibacterial agents for dual action studies, a variety of aryl group-substituted 2-aryl-5-nitro-1H-indoles were synthesized and the activity of the compounds assessed as inhibitors of the NorA multidrug resistance pump in the bacterium Staphylococcus aureus. The NorA protein from the major facilitator superfamily of efflux pumps confers resistance to a variety of structurally dissimilar antimicrobials such as norfloxacin, ethidium bromide, berberine and acrillavin. The compound [4-benzyloxy-2-(5-nitro-1H-2-yl)-phenyl]-methanol was the most potent pump inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.019

文献信息

• Synthesis of functionalised 2-aryl-5-nitro-1H-indoles and their activity as bacterial NorA efflux pump inhibitors
  作者：Siritron Samosorn、John B. Bremner、Anthony Ball、Kim Lewis

  DOI：10.1016/j.bmc.2005.09.019

  日期：2006.2

  In order to develop structure-activity relationships and to provide access to antibacterial agents for dual action studies, a variety of aryl group-substituted 2-aryl-5-nitro-1H-indoles were synthesized and the activity of the compounds assessed as inhibitors of the NorA multidrug resistance pump in the bacterium Staphylococcus aureus. The NorA protein from the major facilitator superfamily of efflux pumps confers resistance to a variety of structurally dissimilar antimicrobials such as norfloxacin, ethidium bromide, berberine and acrillavin. The compound [4-benzyloxy-2-(5-nitro-1H-2-yl)-phenyl]-methanol was the most potent pump inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.