methyl 3-nitro-9-oxoacridan-5-carboxylate | 86611-45-2

• 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: methyl 3-nitro-9-oxoacridan-5-carboxylate
• 英文别名: methyl 3-nitro-acridone-5-carboxylate；Methyl 6-nitro-9(10H)-acridanone-4-carboxylate；methyl 6-nitro-9-oxo-10H-acridine-4-carboxylate
• CAS: 86611-45-2
• 化学式: C₁₅H₁₀N₂O₅
• 分子量: 298.255
• InChiKey: NXHMBAGVAXZGOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-nitro-9-oxoacridan-5-carboxylate 在 氯化亚砜 、 硫酸 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 9-Chloro-6-nitro-acridine-4-carboxylic acid methylamide
  参考文献：
  名称：

  Potential antitumor agents. Part 38. 3-Substituted 5-carboxamido derivatives of amsacrine

  摘要：

  The synthesis and biological evaluation of a series of 3-substituted 5-carboxamido derivatives of amsacrine (m-AMSA) are described. This series was developed as the result of previous quantitative structure-activity relationship (QSAR) studies of the antitumor activity of 9-anilinoacridine derivatives. In agreement with these studies, this class of compounds, possessing a variety of small nonpolar groups at the 3-position, together with very hydrophilic carboxamido groups at the 5-position, have high in vivo activity against animal leukemia models.

  DOI：

  10.1021/jm00365a013
• 作为产物：
  描述：

  2-氯-4-硝基苯甲酸 以 氯仿 为溶剂， 反应 1.0h， 生成 methyl 3-nitro-9-oxoacridan-5-carboxylate
  参考文献：
  名称：

  The Synthesis of Substituted 9-Oxoacridan-4-carboxylic Acids; Part 3. The Reaction of Methyl Anthranilates with Diphenyliodonium-2-carboxylates

  摘要：

  DOI：

  10.1055/s-1985-31165

文献信息

• Combining G-Quadruplex Targeting Motifs on a Single Peptide Nucleic Acid Scaffold: A Hybrid (3+1) PNA-DNA Bimolecular Quadruplex
  作者：Alexis Paul、Poulami Sengupta、Yamuna Krishnan、Sylvain Ladame

  DOI：10.1002/chem.200800605

  日期：2008.9.26

  We describe the first G-quadruplex targeting approach that combines intercalation and hybridization strategies by investigating the interaction of a G-rich peptide nucleic acid (PNA) acridone conjugate 1 with a three-repeat fragment of the human telomere G 3 to form a hybrid PNA-DNA quadruplex that mimicks the biologically relevant (3+1) pure DNA dimeric telomeric quadruplex. Using a combination of

  我们通过研究富G肽核酸（PNA）cri啶酮共轭物1与人类端粒G 3的三重复片段的相互作用，描述了结合插入和杂交策略的第一种G-四链体靶向方法-模仿生物学相关（3 + 1）纯DNA二聚体端粒四链体的DNA四链体。使用紫外线和荧光光谱，圆二色性（CD）和质谱的组合，我们显示PNA 1甚至可以在与单链三重复片段相互作用的低盐浓度下诱导双分子杂化四链体的形成。的端粒DNA。但是，PNA 1不能侵入B-DNA的短片段，即使后者包含与PNA序列互补的CCC基序。
• DENNY, W. A.;ATWELL, G. J.;BAGULEY, B. C., J. MED. CHEM., 1983, 26, N 11, 1619-1625
  作者：DENNY, W. A.、ATWELL, G. J.、BAGULEY, B. C.

  DOI：——

  日期：——
• Potential antitumor agents. Part 38. 3-Substituted 5-carboxamido derivatives of amsacrine
  作者：William A. Denny、Graham J. Atwell、Bruce C. Baguley

  DOI：10.1021/jm00365a013

  日期：1983.11

  The synthesis and biological evaluation of a series of 3-substituted 5-carboxamido derivatives of amsacrine (m-AMSA) are described. This series was developed as the result of previous quantitative structure-activity relationship (QSAR) studies of the antitumor activity of 9-anilinoacridine derivatives. In agreement with these studies, this class of compounds, possessing a variety of small nonpolar groups at the 3-position, together with very hydrophilic carboxamido groups at the 5-position, have high in vivo activity against animal leukemia models.
• The Synthesis of Substituted 9-Oxoacridan-4-carboxylic Acids; Part 3. The Reaction of Methyl Anthranilates with Diphenyliodonium-2-carboxylates
  作者：Gordon W. Rewcastle、William A. Denny

  DOI：10.1055/s-1985-31165

  日期：——