N,N'-((2S,2'S)-((3,6-dimethylacridine-2,7-diyl)bis(azanediyl))bis(1-oxopropane-1,2-diyl))bis(2-oxo-2H-chromene-3-carboxamide) | 1452831-85-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-((2S,2'S)-((3,6-dimethylacridine-2,7-diyl)bis(azanediyl))bis(1-oxopropane-1,2-diyl))bis(2-oxo-2H-chromene-3-carboxamide)
• CAS: 1452831-85-4
• 化学式: C₄₁H₃₃N₅O₈
• 分子量: 723.742
• InChiKey: ZMFAEGYOCNBIHP-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  54.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  189.71
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  、 N,N'-((2S,2'S)-((3,6-dimethylacridine-2,7-diyl)bis(azanediyl))bis(1-oxopropane-1,2-diyl))bis(2-oxo-2H-chromene-3-carboxamide) 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Novel emissive bio-inspired non-proteinogenic coumarin-alanine amino acid: fluorescent probe for polyfunctional systems

  摘要：

  Two new bio-inspired non-proteinogenic compounds L1 and L2, containing coumarin and/or acridine chromophores and bearing as spacer an alanine amino acid were successfully synthesized and fully characterized by elemental analysis, H-1 and C-13 NMR, infrared spectroscopy (KBr discs), melting point, ESI-TOF (electrospray ionization-time of flight-mass), UV-vis absorption and emission spectroscopy, fluorescence quantum yields and lifetime measurements. A relative fluorescence quantum yield of 0.02 was determined for both compounds. In L2 the presence of an intramolecular energy transfer from the coumarin to the acridine unit was observed. L1 and L2 are quite sensitive to the basicity of the environment. At alkaline values both compounds show a strong quenching in the fluorescence emission, attributed to the photoinduced electron transfer (PET). However, both deprotonated forms recover the emission with the addition of Zn2+, Cd2+ and Al3+ metal ions. As multifunctional emissive probes, the titration of L1 and L2 with lanthanides (III), Eu3+ and Tb3+ was also explored as new visible bio-probes in the absence and in the presence of liposomes. In a liposomal environment a lower energy transfer was observed.

  DOI：

  10.1007/s00726-012-1262-6
• 作为产物：
  描述：

  methyl-2-[(2-oxo-2H-1-benzopyran-3-carbonyl)amino]propanoate 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 N,N'-((2S,2'S)-((3,6-dimethylacridine-2,7-diyl)bis(azanediyl))bis(1-oxopropane-1,2-diyl))bis(2-oxo-2H-chromene-3-carboxamide)
  参考文献：
  名称：

  Novel emissive bio-inspired non-proteinogenic coumarin-alanine amino acid: fluorescent probe for polyfunctional systems

  摘要：

  Two new bio-inspired non-proteinogenic compounds L1 and L2, containing coumarin and/or acridine chromophores and bearing as spacer an alanine amino acid were successfully synthesized and fully characterized by elemental analysis, H-1 and C-13 NMR, infrared spectroscopy (KBr discs), melting point, ESI-TOF (electrospray ionization-time of flight-mass), UV-vis absorption and emission spectroscopy, fluorescence quantum yields and lifetime measurements. A relative fluorescence quantum yield of 0.02 was determined for both compounds. In L2 the presence of an intramolecular energy transfer from the coumarin to the acridine unit was observed. L1 and L2 are quite sensitive to the basicity of the environment. At alkaline values both compounds show a strong quenching in the fluorescence emission, attributed to the photoinduced electron transfer (PET). However, both deprotonated forms recover the emission with the addition of Zn2+, Cd2+ and Al3+ metal ions. As multifunctional emissive probes, the titration of L1 and L2 with lanthanides (III), Eu3+ and Tb3+ was also explored as new visible bio-probes in the absence and in the presence of liposomes. In a liposomal environment a lower energy transfer was observed.

  DOI：

  10.1007/s00726-012-1262-6