[4-(Acridin-9-ylamino)-benzyl]-phosphonic acid dimethyl ester; hydrochloride | 82720-38-5

• 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: [4-(Acridin-9-ylamino)-benzyl]-phosphonic acid dimethyl ester; hydrochloride
• CAS: 82720-38-5
• 化学式: C₂₂H₂₁N₂O₃P*ClH
• 分子量: 428.855
• InChiKey: XUSYINJIBGYXMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.45
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  dimethyl (4-nitrobenzyl)phosphonate 在 palladium on activated charcoal ammonium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 [4-(Acridin-9-ylamino)-benzyl]-phosphonic acid dimethyl ester; hydrochloride
  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