9-(phenylamino)acridine-4-carboxylic acid | 278806-95-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-(phenylamino)acridine-4-carboxylic acid
• 英文别名: 9-anilinoacridine-4-carboxylic acid；9-Anilino-4-carboxyacridine
• CAS: 278806-95-4
• 化学式: C₂₀H₁₄N₂O₂
• 分子量: 314.343
• InChiKey: DLKNUYQXURYTSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(phenylamino)acridine-4-carboxylic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 (glycine-alanine-alanine)-9-anilinoacridine-4-carboxamide
  参考文献：
  名称：

  Solid-Phase Synthesis of Acridine−Peptide Conjugates and Their Analysis by Tandem Mass Spectrometry

  摘要：

  [GRAPHICS]A novel and high-yielding synthesis of 9-anilinoacridine-4-carboxylic acid is reported. This acid has been used in the solid-phase synthesis of a small combinatorial library of acridine-peptide conjugates, Tandem mass spectrometry IES (ES-MS/MS) can be used for structure determination of these compounds at a sensitivity of similar to 10 pmol. This work makes possible the generation of acridine-peptide libraries for the discovery of structure-specific nucleic acid ligands via affinity chromatography selection with mass spectrometric detection.

  DOI：

  10.1021/ol005809v
• 作为产物：
  描述：

  iso-propyl-9(10H)-acridone-4-carboxylate 在 lithium hydroxide 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 132.5h， 生成 9-(phenylamino)acridine-4-carboxylic acid
  参考文献：
  名称：

  Solid-Phase Synthesis of Acridine−Peptide Conjugates and Their Analysis by Tandem Mass Spectrometry

  摘要：

  [GRAPHICS]A novel and high-yielding synthesis of 9-anilinoacridine-4-carboxylic acid is reported. This acid has been used in the solid-phase synthesis of a small combinatorial library of acridine-peptide conjugates, Tandem mass spectrometry IES (ES-MS/MS) can be used for structure determination of these compounds at a sensitivity of similar to 10 pmol. This work makes possible the generation of acridine-peptide libraries for the discovery of structure-specific nucleic acid ligands via affinity chromatography selection with mass spectrometric detection.

  DOI：

  10.1021/ol005809v

文献信息

• 9-Amino Acridines Undergo Reversible Amine Exchange Reactions in Water: Implications on Their Mechanism of Action in Vivo
  作者：Alexis Paul、Sylvain Ladame

  DOI：10.1021/ol9019925

  日期：2009.11.5

  9-Amino substituted acridines undergo a reversible amine exchange reaction in water under near-physiological conditions via an unstable hemiaminal intermediate. This thermodynamically controlled reaction may have implications in understanding the mode of action of 9-aminoacridines in vivo and in the future design of drugs based on this scaffold.

  9-氨基取代的cr啶在近乎生理条件下通过不稳定的半胱氨酸中间体在水中进行可逆的胺交换反应。这种热力学控制的反应可能对理解9-氨基ac啶在体内的作用方式以及未来基于该支架的药物设计有影响。
• Solid-Phase Synthesis of Acridine−Peptide Conjugates and Their Analysis by Tandem Mass Spectrometry
  作者：Coby B. Carlson、Peter A. Beal

  DOI：10.1021/ol005809v

  日期：2000.5.1

  [GRAPHICS]A novel and high-yielding synthesis of 9-anilinoacridine-4-carboxylic acid is reported. This acid has been used in the solid-phase synthesis of a small combinatorial library of acridine-peptide conjugates, Tandem mass spectrometry IES (ES-MS/MS) can be used for structure determination of these compounds at a sensitivity of similar to 10 pmol. This work makes possible the generation of acridine-peptide libraries for the discovery of structure-specific nucleic acid ligands via affinity chromatography selection with mass spectrometric detection.