p-nitrophenyl 3-methyl-9-oxoacridan-5-carboxylate | 78847-68-4

• 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: p-nitrophenyl 3-methyl-9-oxoacridan-5-carboxylate
• 英文别名: 3-Methyl-5-(4-nitrophenoxycarbonyl)-9(10H)acridone；(4-nitrophenyl) 6-methyl-9-oxo-10H-acridine-4-carboxylate
• CAS: 78847-68-4
• 化学式: C₂₁H₁₄N₂O₅
• 分子量: 374.353
• InChiKey: QRNNIAIUXGHZQF-UHFFFAOYSA-N

物化性质

• 熔点：
  279-281 °C
• 沸点：
  619.2±55.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl 3-methyl-9-oxoacridan-5-carboxylate 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 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 、 硫酸 、 铜 、 potassium carbonate 、 三氯化磷 作用下， 以 乙二醇乙醚 为溶剂， 反应 2.5h， 生成 p-nitrophenyl 3-methyl-9-oxoacridan-5-carboxylate
  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

• Compounds having antitumour properties, process for their preparation, these compounds for use as antitumour agents and pharmaceutical compositions containing them
  申请人：DEVELOPMENT FINANCE CORPORATION OF NEW ZEALAND

  公开号：EP0025705A1

  公开（公告）日：1981-03-25

  Compounds represented by the general formula in which R1 represents-CH3, -CH2CH3 or -(CH2)2 CH3; R2 represents -CONHR4, -F, -Cl, -Br, -I, -CF3, -N02, -NH2, -CH3, -OCH3 or-NHCOCH3, and R3 represents -CONHR4, -H, -CH3 or -OCH3, with the proviso that at least one of R2 and R3 represents -CONHR4; and R4 represents H, or -CH3, -CH2CH3, -(CH2)2CH3, -(CH2)3CH3 or - CH2CH(CH3)2, each optionally substituted with hydroxyl, amine and/or amide functions; and acid addition salts thereof have antitumour properties.

  由通式表示的化合物 其中 R1 代表-CH3、-CH2CH3 或-(CH2)2 CH3； R2 代表-CONHR4、-F、-Cl、-Br、-I、 -CF3、-N02、-NH2、-CH3、-OCH3 或-NHCOCH3，以及 R3 代表-CONHR4、-H、-CH3 或-OCH3，但 R2 和 R3 中至少有一个代表-CONHR4； 和 R4 代表 H、或-CH3、-CH2CH3、-(CH2)2CH3、-(CH2)3CH3 或-CH2CH(CH3)2，各自任选被羟基、胺和/或酰胺官能团取代； 及其酸加成盐具有抗肿瘤特性。
• 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：——
• US4472582A
  申请人：——

  公开号：US4472582A

  公开（公告）日：1984-09-18
• 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.