tert-butyl (3-((N-(3-((N-(3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)propyl)-2-nitrophenyl)sulfonamido)propyl)-2-nitrophenyl)sulfonamido)propyl)carbamate | 1380167-29-2

• 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: tert-butyl (3-((N-(3-((N-(3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)propyl)-2-nitrophenyl)sulfonamido)propyl)-2-nitrophenyl)sulfonamido)propyl)carbamate
• CAS: 1380167-29-2
• 化学式: C₃₂H₄₂N₈O₁₂S₂
• 分子量: 794.864
• InChiKey: FHKUOSOTYGMPMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  54.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  263.36
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3-((N-(3-((N-(3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)propyl)-2-nitrophenyl)sulfonamido)propyl)-2-nitrophenyl)sulfonamido)propyl)carbamate 在 盐酸 、 potassium carbonate 、 苯硫酚 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.5h， 生成 4-Amino-1-[3-[3-(3-aminopropylamino)propylamino]propyl]pyrimidin-2-one;hydrochloride
  参考文献：
  名称：

  Synthesis and binding properties of new selective ligands for the nucleobase opposite the AP site

  摘要：

  DNA is continuously damaged by endogenous and exogenous factors such as oxidative stress or DNA alkylating agents. These damaged nucleobases are removed by DNA N-glycosylase and form apurinic/apyrimidinic sites (AP sites) as intermediates in the base excision repair (BER) pathway. AP sites are also representative DNA damages formed by spontaneous hydrolysis. The AP sites block DNA polymerase and a mismatch nucleobase is inserted opposite the AP sites by polymerization to cause acute toxicities and mutations. Thus, AP site specific compounds have attracted much attention for therapeutic and diagnostic purposes. In this study, we have developed nucleobase-polyamine conjugates as the AP site binding ligand by expecting that the nucleobase part would play a role in the specific recognition of the nucleobase opposite the AP site by the Watson-Crick base pair formation and that the polyamine part should contribute to the access of the ligand to the AP site by a non-specific interaction to the DNA phosphate backbone. The nucleobase conjugated with 3,3'-diaminodipropylamine (A-ligand, G-ligand, C-ligand, T-ligand and U-ligand) showed a specific stabilization of the duplex containing the AP site depending on the complementary combination with the nucleobase opposite the AP site; that is A-ligand to T, G-ligand to C, C-ligand to G, T- and U-ligand to A. The thermodynamic binding parameters clearly indicated that the specific stabilization is due to specific binding of the ligands to the complementary AP site. These results have suggested that the complementary base pairs of the Watson-Crick type are formed at the AP site. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.009
• 作为产物：
  描述：

  叔丁氧羰基-3,3'-亚氨基二丙胺 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 153.5h， 生成 tert-butyl (3-((N-(3-((N-(3-(4-acetamido-2-oxopyrimidin-1(2H)-yl)propyl)-2-nitrophenyl)sulfonamido)propyl)-2-nitrophenyl)sulfonamido)propyl)carbamate
  参考文献：
  名称：

  Synthesis and binding properties of new selective ligands for the nucleobase opposite the AP site

  摘要：

  DNA is continuously damaged by endogenous and exogenous factors such as oxidative stress or DNA alkylating agents. These damaged nucleobases are removed by DNA N-glycosylase and form apurinic/apyrimidinic sites (AP sites) as intermediates in the base excision repair (BER) pathway. AP sites are also representative DNA damages formed by spontaneous hydrolysis. The AP sites block DNA polymerase and a mismatch nucleobase is inserted opposite the AP sites by polymerization to cause acute toxicities and mutations. Thus, AP site specific compounds have attracted much attention for therapeutic and diagnostic purposes. In this study, we have developed nucleobase-polyamine conjugates as the AP site binding ligand by expecting that the nucleobase part would play a role in the specific recognition of the nucleobase opposite the AP site by the Watson-Crick base pair formation and that the polyamine part should contribute to the access of the ligand to the AP site by a non-specific interaction to the DNA phosphate backbone. The nucleobase conjugated with 3,3'-diaminodipropylamine (A-ligand, G-ligand, C-ligand, T-ligand and U-ligand) showed a specific stabilization of the duplex containing the AP site depending on the complementary combination with the nucleobase opposite the AP site; that is A-ligand to T, G-ligand to C, C-ligand to G, T- and U-ligand to A. The thermodynamic binding parameters clearly indicated that the specific stabilization is due to specific binding of the ligands to the complementary AP site. These results have suggested that the complementary base pairs of the Watson-Crick type are formed at the AP site. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.009