3-(3',5'-di-O-tert-butyldimethylsilyl-D-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-O-trifluoromethylsulfonyl-2-oxophenoxadine | 1332507-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3',5'-di-O-tert-butyldimethylsilyl-D-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-O-trifluoromethylsulfonyl-2-oxophenoxadine
• 英文别名: [3-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-2-oxo-9-[2-(phenylmethoxycarbonylamino)ethoxy]-10H-pyrimido[5,4-b][1,4]benzoxazin-7-yl] trifluoromethanesulfonate
• CAS: 1332507-58-0
• 化学式: C₃₈H₅₃F₃N₄O₁₁SSi₂
• 分子量: 887.091
• InChiKey: BQCDQQVXYHEXNI-MAJWKWKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.33
• 重原子数：
  59
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3-(3',5'-di-O-tert-butyldimethylsilyl-D-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-O-trifluoromethylsulfonyl-2-oxophenoxadine 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tripotassium phosphate "n" hydrate 、 palladium diacetate 、 溶剂黄146 、 三乙胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 2.0h， 生成
  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 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 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 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 125.5h， 生成 3-(3',5'-di-O-tert-butyldimethylsilyl-D-ribofuranosyl)-9-(2-N-benzylcarbamyl-ethoxy)-1,3-diaza-7-O-trifluoromethylsulfonyl-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

文献信息

• Optimization of fluorescence property of the 8-oxodGclamp derivative for better selectivity for 8-oxo-2′-deoxyguanosine
  作者：Yohei Koga、Yasufumi Fuchi、Osamu Nakagawa、Shigeki Sasaki

  DOI：10.1016/j.tet.2011.03.111

  日期：2011.9

  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.