N-[4-(2-N-benzylcarbamylethoxy-6-hydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine | 1332507-66-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N-[4-(2-N-benzylcarbamylethoxy-6-hydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine
• CAS: 1332507-66-0
• 化学式: C₃₀H₃₅BrN₄O₁₀
• 分子量: 691.533
• InChiKey: QHVMIBHKEINORJ-TUACAJSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  45.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  190.7
• 氢给体数：
  5.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N-[4-(2-N-benzylcarbamylethoxy-6-hydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 54.0h， 以48%的产率得到3-(2'-deoxy-D-ribofuranosyl)-9-(2-N-benzylcarbamylethoxy)-1,3-diaza-7-O-pivaloyl-2-oxophenoxadine
  参考文献：
  名称：

  Optimization of fluorescence property of the 8-oxodGclamp derivative for better selectivity for 8-oxo-2′-deoxyguanosine

  摘要：

  2'-Deoxyguanosine (dG) suffers from oxidation by reactive oxygen species (ROS) to form 8-oxo-2'-deoxyguanosine (8-oxo-dG), which is regarded as a marker of oxidative stress in the cells. In our continuous study for the recognition molecule of 8-oxo-dG, 8-oxoGclamp and its derivatives have been identified as the selective fluorescent probe. However, it is an obstacle for further application that dG also forms a complex with 8-oxoGclamp. resulting in fluorescence quenching in less polar solvents. Quenching of the fluorescence of 8-oxoGclamp is thought to involve photo-induced electron transfer in the complex. It was hypothesized that the energy level of the excited state of 8-oxoGclamp and the HOMO energy of dG are the preliminary determinant of the quenching efficiency. Thus, fluorescence properties of the substituted derivatives at the 7-position of the 1,3-diazaphenoxazine part of 8-oxoGclamp were investigated. Among the new derivatives, fluorescence of the 7-phenyl substituted 8-oxoGclamp was not quenched by dG even in the stable complex, exhibiting the highest selectivity for 8-oxo-dG. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.111
• 作为产物：
  描述：

  4-O-pivaloyl-2-aminophloroglucinol 在 偶氮二甲酸二异丙酯 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 N-[4-(2-N-benzylcarbamylethoxy-6-hydroxy-4-O-pivaloylphenyl)]-2'-deoxy-5-bromouridine
  参考文献：
  名称：

  Optimization of fluorescence property of the 8-oxodGclamp derivative for better selectivity for 8-oxo-2′-deoxyguanosine

  摘要：

  2'-Deoxyguanosine (dG) suffers from oxidation by reactive oxygen species (ROS) to form 8-oxo-2'-deoxyguanosine (8-oxo-dG), which is regarded as a marker of oxidative stress in the cells. In our continuous study for the recognition molecule of 8-oxo-dG, 8-oxoGclamp and its derivatives have been identified as the selective fluorescent probe. However, it is an obstacle for further application that dG also forms a complex with 8-oxoGclamp. resulting in fluorescence quenching in less polar solvents. Quenching of the fluorescence of 8-oxoGclamp is thought to involve photo-induced electron transfer in the complex. It was hypothesized that the energy level of the excited state of 8-oxoGclamp and the HOMO energy of dG are the preliminary determinant of the quenching efficiency. Thus, fluorescence properties of the substituted derivatives at the 7-position of the 1,3-diazaphenoxazine part of 8-oxoGclamp were investigated. Among the new derivatives, fluorescence of the 7-phenyl substituted 8-oxoGclamp was not quenched by dG even in the stable complex, exhibiting the highest selectivity for 8-oxo-dG. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.111