4-((1-(4-benzoylphenyl)-1-oxo-6,9,12-trioxa-2-azapentadecan-15-yl)amino)-N2,N6-di(quinolin-3-yl)pyridine-2,6-dicarboxamide | 1592668-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-((1-(4-benzoylphenyl)-1-oxo-6,9,12-trioxa-2-azapentadecan-15-yl)amino)-N2,N6-di(quinolin-3-yl)pyridine-2,6-dicarboxamide
• CAS: 1592668-52-4
• 化学式: C₄₉H₄₇N₇O₇
• 分子量: 845.955
• InChiKey: GGCBHYKNPJQBIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.59
• 重原子数：
  63.0
• 可旋转键数：
  22.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  182.76
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  4-((1-(4-benzoylphenyl)-1-oxo-6,9,12-trioxa-2-azapentadecan-15-yl)amino)-N2,N6-di(quinolin-3-yl)pyridine-2,6-dicarboxamide 、 碘甲烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以68%的产率得到3,3'-((4-((1-(4-benzoylphenyl)-1-oxo-6,9,12-trioxa-2-azapentadecan-15-yl)amino)pyridine-2,6-dicarbonyl)bis(azanediyl))bis(1-methylquinolin-1-ium) iodide
  参考文献：
  名称：

  Photo-Cross-Linking Probes for Trapping G-Quadruplex DNA

  摘要：

  AbstractWe have developed a straightforward synthetic pathway to a set of six photoactivatable G‐quadruplex ligands with a validated G4‐binding motif (the bisquinolinium pyridodicarboxamide PDC‐360A) tethered through various spacers to two different photo‐cross‐linking groups: benzophenone and an aryl azide. The high quadruplex‐versus‐duplex selectivity of the PDC core was retained in the new derivatives and resulted in selective alkylation of two well‐known G‐quadruplexes (human telomeric G4 and oncogene promoter c‐myc G4) under conditions of harsh competition. The presence of two structurally different photoactivatable functions allowed the selective alkylation of G‐quadruplex structures at specific nucleobases and irreversible G4 binding. The topology and sequence of the quadruplex matrix appear to influence strongly the alkylation profile, which differs for the telomeric and c‐myc quadruplexes. The new compounds are photoactive in cells and thus provide new tools for studying G4 biology.

  DOI：

  10.1002/anie.201307413
• 作为产物：
  描述：

  N-Boc-4,7,10-三氧杂-1,13-十三烷二胺 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 4-((1-(4-benzoylphenyl)-1-oxo-6,9,12-trioxa-2-azapentadecan-15-yl)amino)-N2,N6-di(quinolin-3-yl)pyridine-2,6-dicarboxamide
  参考文献：
  名称：

  Photo-Cross-Linking Probes for Trapping G-Quadruplex DNA

  摘要：

  AbstractWe have developed a straightforward synthetic pathway to a set of six photoactivatable G‐quadruplex ligands with a validated G4‐binding motif (the bisquinolinium pyridodicarboxamide PDC‐360A) tethered through various spacers to two different photo‐cross‐linking groups: benzophenone and an aryl azide. The high quadruplex‐versus‐duplex selectivity of the PDC core was retained in the new derivatives and resulted in selective alkylation of two well‐known G‐quadruplexes (human telomeric G4 and oncogene promoter c‐myc G4) under conditions of harsh competition. The presence of two structurally different photoactivatable functions allowed the selective alkylation of G‐quadruplex structures at specific nucleobases and irreversible G4 binding. The topology and sequence of the quadruplex matrix appear to influence strongly the alkylation profile, which differs for the telomeric and c‐myc quadruplexes. The new compounds are photoactive in cells and thus provide new tools for studying G4 biology.

  DOI：

  10.1002/anie.201307413