6-fluoro-3-(1H-imidazo[4,5-f][1,10]-phenanthroline-2-yl)-4H-chromen-4-one | 1257631-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-fluoro-3-(1H-imidazo[4,5-f][1,10]-phenanthroline-2-yl)-4H-chromen-4-one
• CAS: 1257631-53-0
• 化学式: C₂₂H₁₁FN₄O₂
• 分子量: 382.353
• InChiKey: WTVZZVCGTLUPRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  6-氟色同-3-甲醛 、 1,10-邻二氮杂菲-5,6-二酮 在 ammonium acetate 、 溶剂黄146 作用下， 反应 2.0h， 以85%的产率得到6-fluoro-3-(1H-imidazo[4,5-f][1,10]-phenanthroline-2-yl)-4H-chromen-4-one
  参考文献：
  名称：

  Study of the interaction between ruthenium(II) complexes and CT-DNA: synthesis, characterisation, photocleavage and antimicrobial activity studies

  摘要：

  Two polypyridyl ligands 6-fluro-3-(1H-imidazo [4,5-f] [1,10]-phenanthroline-2-yl)-4H-chromen-4-one (FIPC), 6-chloro-3-(1H-imidazo [4,5-f] [1,10]-phenanthroline-2-yl)-4H-chromen-4-one (ClIPC) polypyridyl ligands and their Ru(II) complexes [Ru(bipy)2FIPC]2+(1), [Ru(dmb)2FIPC]2+(2), [Ru(phen)2FIPC]2+(3), [Ru(bipy)2ClIPC]2+(4), [Ru(dmb)2ClIPC]2+(5) and [Ru(phen)2ClIPC]2+(6) ((bipy=2,2'-bipyridine, dmb=4,4'-dimethyl-2,2'-bipyridine and phen=1,10-phenanthroline) have been synthesised and characterised by elemental analysis, Mass spectra, IR, 1H and 13C-NMR. The DNA-binding of the six complexes to calf-thymus DNA (CT-DNA) has been investigated by different spectrophotometric, fluorescence and viscosity measurements. The results suggest that 1-6 complexes bind to CT-DNA through intercalation. The variation in binding affinities of these complexes is rationalised by a consideration of electrostatic, steric factors and nature of ancillary ligands. Under irradiation at 365nm, the three complexes have also been found to promote the photocleavage of plasmid pBR 322 DNA. Inhibitor studies suggest that singlet oxygen (1O2) plays a significant role in the cleavage mechanism of Ru(II) complexes. Thereby, under comparable experimental conditions [Ru(phen)2FIPC]2+(3), [Ru(phen)2ClIPC]2+(6) cleaves DNA more effectively than 1, 2, 4 and 5 complexes do. The Ru(II) polypyridyl complexes (1-6) have been screened for antimicrobial activities.

  DOI：

  10.1080/10610278.2010.510194