9-Chloro-6-methyl-acridine-4-carboxylic acid 4-nitro-phenyl ester | 78847-69-5

• 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: 9-Chloro-6-methyl-acridine-4-carboxylic acid 4-nitro-phenyl ester
• 英文别名: 4-Nitrophenyl 9-chloro-6-methylacridine-4-carboxylate；(4-nitrophenyl) 9-chloro-6-methylacridine-4-carboxylate
• CAS: 78847-69-5
• 化学式: C₂₁H₁₃ClN₂O₄
• 分子量: 392.798
• InChiKey: INEMBLDSWFWQRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-Chloro-6-methyl-acridine-4-carboxylic acid 4-nitro-phenyl ester 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 9-[4-(methanesulfonamido)-2-methoxyanilino]-N,6-dimethylacridine-4-carboxamide
  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-溴-4-甲基苯甲酸 在 吡啶 、 copper(I) oxide 、 氯化亚砜 、 硫酸 、 铜 、 potassium carbonate 、 N,N-二甲基甲酰胺 、 三氯化磷 作用下， 以 乙二醇乙醚 为溶剂， 反应 3.0h， 生成 9-Chloro-6-methyl-acridine-4-carboxylic acid 4-nitro-phenyl ester
  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

文献信息

• 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.