(2-(5-硝基-1H-吲哚-2-基)苯基)甲醇 | 874752-05-3

• 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
• 中文名称: (2-(5-硝基-1H-吲哚-2-基)苯基)甲醇
• 英文名称: (2-(5-nitro-1H-indol-2-yl)phenyl)methanol
• 英文别名: [2-(5-nitro-1H-indol-2-yl)phenyl]methanol
• CAS: 874752-05-3
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: AEWWEYQTIRUIET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-(5-硝基-1H-吲哚-2-基)苯基)甲醇 在 四氯化碳 、 sodium azide 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以74%的产率得到2-[2-(azidomethyl)phenyl]-5-nitro-1H-indole
  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 、 硼烷四氢呋喃络合物 、 potassium tert-butylate 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 25.0h， 生成 (2-(5-硝基-1H-吲哚-2-基)苯基)甲醇
  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 and Structural Characterization of 1-[2-(5-Nitro-1H-indol-2-yl)phenyl]methylpyridinium Chloride
  作者：John B. Bremner、Siritron Samosorn、Brian W. Skelton、Allan H. White

  DOI：10.3390/molecules16097627

  日期：——

  incorporating 2-aryl-5-nitro-1H-indole moieties as potential bacterial NorA efflux pump inhibitors, the compound 1-[2-(5-nitro-1H-indol-2-yl)phenyl]methylpyridinium chloride (2) was synthesized and structurally characterized. This pyridinium chloride salt crystallized in the monoclinic space group P2(1)/c with the following unit cell dimensions: a 10.274(3) Å, b 13.101(4) Å, c 13.439(4) Å, b 107.702(7)°, V

  在结合 2-芳基-5-硝基-1H-吲哚部分作为潜在细菌 NorA 外排泵抑制剂的杂化抗菌剂的研究过程中，化合物 1-[2-(5-硝基-1H-吲哚-2-基)苯基] 甲基吡啶鎓氯化物 (2) 已合成并进行结构表征。这种氯化吡啶盐在单斜空间群 P2(1)/c 中结晶，具有以下晶胞尺寸：a 10.274(3) Å, b 13.101(4) Å, c 13.439(4) Å, b 107.702(7)° , V 1723.2(9) ų, Z (fu) = 4; R1 = 0.048，wR2 = 0.13。单晶 X 射线结构中令人感兴趣的是吡啶鎓平面在吲哚杂环残基上的（分子内）布置 [平面二面角 17.91(4)°]。
• Structure–activity relationships of 2-aryl-1H-indole inhibitors of the NorA efflux pump in Staphylococcus aureus
  作者：Joseph I. Ambrus、Michael J. Kelso、John B. Bremner、Anthony R. Ball、Gabriele Casadei、Kim Lewis

  DOI：10.1016/j.bmcl.2008.06.093

  日期：2008.8

  The synthesis of 22 2-aryl-1H-indoles, including 12 new compounds, has been achieved via Pd- or Rh-mediated methodologies, or selective electrophilic substitution. All three methods were based on elaborations from simple indole precursors. SAR studies on these indoles and 2-phenyl-1H-indole in Staphylococcus aureus as NorA efflux pump inhibitors indicated 5-nitro-2-(3-methoxycarbonyl)phenyl-1H-indole was a slightly more potent inhibitor than the lead INF55. A promising new antibacterial lead compound against S. aureus (2-phenyl-1H-indol-5-yl)-methanol, was also found. (c) 2008 Elsevier Ltd. All rights reserved.