4-amino-3-[2-[3-[2-[2-amino-5-[3-(dimethylamino)propylcarbamoyl]phenyl]ethynyl]phenyl]ethynyl]-N-[3-(dimethylamino)propyl]benzamide | 1085359-42-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4-amino-3-[2-[3-[2-[2-amino-5-[3-(dimethylamino)propylcarbamoyl]phenyl]ethynyl]phenyl]ethynyl]-N-[3-(dimethylamino)propyl]benzamide
• CAS: 1085359-42-7
• 化学式: C₃₄H₄₀N₆O₂
• 分子量: 564.731
• InChiKey: ROKKNOFQSSZPJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,3'-(1,3-phenylenebis(ethyne-2,1-diyl))bis(4-aminobenzoic acid) 、 N,N-二甲基-1,3-二氨基丙烷 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以87%的产率得到4-amino-3-[2-[3-[2-[2-amino-5-[3-(dimethylamino)propylcarbamoyl]phenyl]ethynyl]phenyl]ethynyl]-N-[3-(dimethylamino)propyl]benzamide
  参考文献：
  名称：

  Diarylethynyl Amides That Recognize the Parallel Conformation of Genomic Promoter DNA G-Quadruplexes

  摘要：

  We report bis-phenylethynyl amide derivatives as a potent G-quadruplex binding small molecule scaffold. The amide derivatives were efficiently prepared in 3 steps by employing Sonogashira coupling, ester hydrolysis and a chemoselective amide coupling. Ligand-quadruplex recognition has been evaluated using a fluorescence resonance energy transfer (FRET) melting assay, surface plasmon resonance (SPR), circular dichroism (CD) and H-1 nuclear magnetic resonance (NMR) spectroscopy. While most of the G-quadruplex ligands reported so far comprise a planar, aromatic core designed to stack on the terminal tetrads of a G-quadruplex, these compounds are neither polycyclic, nor macrocyclic and have free rotation around the triple bond enabling conformational flexibility. Such molecules show very good binding affinity, excellent quadruplex:duplex selectivity and also promising discrimination between intramolecular promoter quadruplexes. Our results indicate that the recognition of the c-kit2 quadruplex by these ligands is achieved through groove binding, which favors the formation of a parallel conformation.

  DOI：

  10.1021/ja8046552