N-Acridin-9-yl-N'-(2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-2-yl)-benzene-1,4-diamine | 82720-29-4

• 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: N-Acridin-9-yl-N'-(2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-2-yl)-benzene-1,4-diamine
• 英文别名: 1-N-acridin-9-yl-4-N-(2-oxo-1,3,2lambda5-oxazaphosphinan-2-yl)benzene-1,4-diamine；1-N-acridin-9-yl-4-N-(2-oxo-1,3,2λ5-oxazaphosphinan-2-yl)benzene-1,4-diamine
• CAS: 82720-29-4
• 化学式: C₂₂H₂₁N₄O₂P
• 分子量: 404.408
• InChiKey: FELLJVHKWWSNRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  75.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4-硝基苯基)-氨基甲酸苯甲酯 在 吡啶 、 盐酸 、 ammonium hydroxide 、 铁粉 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 N-Acridin-9-yl-N'-(2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-2-yl)-benzene-1,4-diamine
  参考文献：
  名称：

  Potential antitumor agents. 37. Organophosphorus derivatives of 9-anilinoacridine

  摘要：

  A series of 9-anilinoacridine derivatives substituted in the anilino ring with a variety of phosphoramide and related substitutents has been prepared, and the antitumor activity has been evaluated both in vivo and in vitro against the L1210 or P-388 mouse leukemia systems. The DNA-binding properties were measured using the ethidium displacement method, and the structural requirements for strong binding were found to differ from those for antileukemic activity. For high biological activity a marked preference for oxygen-containing substituents on the phosphorus atom was noted, while for high DNA binding a requirement for nitrogen-containing or cyclized substituents was observed. The most active congeners, as assayed in both in vitro and in vivo systems, were comparable in activity to the clinically utilized anilinoacridine derivative N-[4'-(9-acridinylamino)-3'-methoxyphenyl]methanesulfonamide (m-AMSA, amsacrine).

  DOI：

  10.1021/jm00352a027

文献信息

• REWCASTLE, G. W.;BAGULEY, B. C.;CAIN, B. F., J. MED. CHEM., 1982, 25, N 10, 1231-1235
  作者：REWCASTLE, G. W.、BAGULEY, B. C.、CAIN, B. F.

  DOI：——

  日期：——
• Potential antitumor agents. 37. Organophosphorus derivatives of 9-anilinoacridine
  作者：Gordon W. Rewcastle、Bruce C. Baguley、Bruce F. Cain

  DOI：10.1021/jm00352a027

  日期：1982.10

  A series of 9-anilinoacridine derivatives substituted in the anilino ring with a variety of phosphoramide and related substitutents has been prepared, and the antitumor activity has been evaluated both in vivo and in vitro against the L1210 or P-388 mouse leukemia systems. The DNA-binding properties were measured using the ethidium displacement method, and the structural requirements for strong binding were found to differ from those for antileukemic activity. For high biological activity a marked preference for oxygen-containing substituents on the phosphorus atom was noted, while for high DNA binding a requirement for nitrogen-containing or cyclized substituents was observed. The most active congeners, as assayed in both in vitro and in vivo systems, were comparable in activity to the clinically utilized anilinoacridine derivative N-[4'-(9-acridinylamino)-3'-methoxyphenyl]methanesulfonamide (m-AMSA, amsacrine).