dimethyl N-{4-[(3-amino-9-acridinyl)amino]phenyl}phosphoramidate | 90171-98-5

• 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: dimethyl N-{4-[(3-amino-9-acridinyl)amino]phenyl}phosphoramidate
• 英文别名: 9-N-[4-(dimethoxyphosphorylamino)phenyl]acridine-3,9-diamine
• CAS: 90171-98-5
• 化学式: C₂₁H₂₁N₄O₃P
• 分子量: 408.396
• InChiKey: JMTZOXWJTNUHAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  98.5
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-4-nitrophenyl-dimethyl phosphoramidic acid ester 在 palladium on activated charcoal 盐酸 、 ammonium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 生成 dimethyl N-{4-[(3-amino-9-acridinyl)amino]phenyl}phosphoramidate
  参考文献：
  名称：

  Potential antitumor agents. 42. Structure-activity relationships for acridine-substituted dimethyl phosphoramidate derivatives of 9-anilinoacridine

  摘要：

  Replacement of the 1'-methanesulfonamide group of the 9-anilinoacridine class of antitumor agents with the 1'-(dimethyl phosphoramidate) group provides compounds that are generally more lipophilic and bind more tightly to DNA. On the average, the dimethyl phosphoramidates are twice as dose potent as the corresponding methanesulfonamide (AMSA) compounds against P388 leukemia in vivo, but also show about twice the acute toxicity and no resultant improvement in tumor cell selectivity (ILSmax values) is seen. A pairwise comparison of a range of acridine-substituted compounds shows that structure-activity relationships within each series are similar and dominated by the acridine substitution pattern.

  DOI：

  10.1021/jm00374a020

文献信息

• Potential antitumor agents. 42. Structure-activity relationships for acridine-substituted dimethyl phosphoramidate derivatives of 9-anilinoacridine
  作者：Gordon W. Rewcastle、Graham J. Atwell、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00374a020

  日期：1984.8

  Replacement of the 1'-methanesulfonamide group of the 9-anilinoacridine class of antitumor agents with the 1'-(dimethyl phosphoramidate) group provides compounds that are generally more lipophilic and bind more tightly to DNA. On the average, the dimethyl phosphoramidates are twice as dose potent as the corresponding methanesulfonamide (AMSA) compounds against P388 leukemia in vivo, but also show about twice the acute toxicity and no resultant improvement in tumor cell selectivity (ILSmax values) is seen. A pairwise comparison of a range of acridine-substituted compounds shows that structure-activity relationships within each series are similar and dominated by the acridine substitution pattern.