8-methyl-2-nitro-7-oxo-8,11-dihydro-7H-5,8,11-triazacyclopenta[b]phenanthrene-9-carboxylic acid | 881922-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-methyl-2-nitro-7-oxo-8,11-dihydro-7H-5,8,11-triazacyclopenta[b]phenanthrene-9-carboxylic acid
• 英文别名: 7H,8,11-triaza-cyclopenta[b]phenanthrene；13-methyl-4-nitro-11-oxo-8,13,17-triazatetracyclo[8.7.0.02,7.012,16]heptadeca-1,3,5,7,9,12(16),14-heptaene-14-carboxylic acid
• CAS: 881922-45-8
• 化学式: C₁₆H₁₀N₄O₅
• 分子量: 338.279
• InChiKey: WKHUBTYIUMANDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-methyl-2-nitro-7-oxo-8,11-dihydro-7H-5,8,11-triazacyclopenta[b]phenanthrene-9-carboxylic acid 、 N,N-二甲基-1,3-二氨基丙烷 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以37%的产率得到8-methyl-2-nitro-7-oxo-8,11-dihydro-7H-5,8,11-triazacyclopenta[b]phenanthrene-9-carboxylic acid N-[3-(dimethylamino)propyl]amide
  参考文献：
  名称：

  Synthesis and testing of a triaza-cyclopenta[b]phenanthrene scaffold as a DNA binding agent

  摘要：

  A novel DNA binding agent based upon a triaza-cyclopenta[b]phenanthrene scaffold, compound 1, has been synthesized. dsDNA binding analysis of this compound using the ethidium bromide displacement assay indicated a preference for GC-rich sequences. However, equilibrium dialysis experiments against a variety of nucleic acids showed that the target compound bound about 20-fold tighter to G-quartet DNA than to dsDNA under physiological salt concentrations. The binding of 1 to G-quartet DNA was verified by the ability Of the Compound to promote the formation of the quartet and to compete with TmPyP4 for binding to the quadruplex. Given the importance of G-quartet binding agents in the treatment of cancer and in the understanding of drug-DNA interactions, 1 and its related analogs should find utility as a new class of G-quartet specific agents. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.047
• 作为产物：
  描述：

  4-氯-6-硝基喹啉-3-羧酸乙酯 在 吡啶 、 sodium hydroxide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 8-methyl-2-nitro-7-oxo-8,11-dihydro-7H-5,8,11-triazacyclopenta[b]phenanthrene-9-carboxylic acid
  参考文献：
  名称：

  Synthesis and testing of a triaza-cyclopenta[b]phenanthrene scaffold as a DNA binding agent

  摘要：

  A novel DNA binding agent based upon a triaza-cyclopenta[b]phenanthrene scaffold, compound 1, has been synthesized. dsDNA binding analysis of this compound using the ethidium bromide displacement assay indicated a preference for GC-rich sequences. However, equilibrium dialysis experiments against a variety of nucleic acids showed that the target compound bound about 20-fold tighter to G-quartet DNA than to dsDNA under physiological salt concentrations. The binding of 1 to G-quartet DNA was verified by the ability Of the Compound to promote the formation of the quartet and to compete with TmPyP4 for binding to the quadruplex. Given the importance of G-quartet binding agents in the treatment of cancer and in the understanding of drug-DNA interactions, 1 and its related analogs should find utility as a new class of G-quartet specific agents. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.047