(4-甲氧基苯基)-(5-硝基吲哚-1-基)甲酮 | 820234-19-3

• 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: (4-甲氧基苯基)-(5-硝基吲哚-1-基)甲酮
• 英文名称: 1-(4-methoxybenzoyl)-5-nitro-1H-indole
• 英文别名: 1H-Indole, 1-(4-methoxybenzoyl)-5-nitro-；(4-methoxyphenyl)-(5-nitroindol-1-yl)methanone
• CAS: 820234-19-3
• 化学式: C₁₆H₁₂N₂O₄
• 分子量: 296.282
• InChiKey: PUSKESRFGYNGBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-甲氧基苯基)-(5-硝基吲哚-1-基)甲酮 在 palladium diacetate 硼烷四氢呋喃络合物 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 30.0h， 生成 [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 、 大茴香酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以95%的产率得到(4-甲氧基苯基)-(5-硝基吲哚-1-基)甲酮
  参考文献：
  名称：

  N-Acylation of 5-Substituted Indoles with Carboxylic Acids via DCC Coupling

  摘要：

  提出了一种使用DCC和DMAP进行N-酰基化反应的方法，用于5-取代吲哚与羧酸的反应。当C-5位置存在吸电子基团时，获得了高产率，然而，对于C-5位置为给电子基团的反应，该方法效果较差。

  DOI：

  10.1055/s-2004-831228

文献信息

• N-Acylation of 5-Substituted Indoles with Carboxylic Acids via DCC Coupling
  作者：John B. Bremner、Siritron Samosorn、Joseph I. Ambrus

  DOI：10.1055/s-2004-831228

  日期：——

  A method for the N-acylation of 5-substituted indoles with carboxylic acids using DCC and DMAP is presented. High yields were obtained when an electron-withdrawing group was present at C-5, however the method was less effective with a C-5 electron-donating group.

  提出了一种使用DCC和DMAP进行N-酰基化反应的方法，用于5-取代吲哚与羧酸的反应。当C-5位置存在吸电子基团时，获得了高产率，然而，对于C-5位置为给电子基团的反应，该方法效果较差。
• COMPOUNDS AND METHODS FOR TREATING PROTEIN FOLDING DISORDERS
  申请人：Carter Michael D.

  公开号：US20100144821A1

  公开（公告）日：2010-06-10

  The invention is directed to compounds and methods for treating protein folder disorders. In certain embodiments the invention provides compounds and methods for treating neurodegenerative diseases such as Alzheimer's disease, tauopathy, cerebral amyloid angiopathy, Lewy body disease, dementia, Huntington's disease and prion-based spongiform encelopathy. The invention further provides compounds, methods and pharmaceutical compositions for inhibiting tau protein, Aβ protein or α-synuclein protein aggregation.

  本发明涉及化合物和方法，用于治疗蛋白质折叠障碍。在某些实施例中，本发明提供了治疗神经退行性疾病，如阿尔茨海默病、tau病、脑淀粉样血管病、Lewy体病、痴呆症、亨廷顿病和基于朊病毒海绵状脑病的化合物和方法。本发明还提供了化合物、方法和制药组合物，用于抑制tau蛋白、Aβ蛋白或α-突触核蛋白的聚集。
• WO2008/58402
  申请人：——

  公开号：——

  公开（公告）日：——
• US8362066B2
  申请人：——

  公开号：US8362066B2

  公开（公告）日：2013-01-29
• 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.