N-[4-(acridin-9-ylamino)-3-(methylamino)phenyl]methanesulfonamide;hydron;chloride | 88412-53-7

• 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-[4-(acridin-9-ylamino)-3-(methylamino)phenyl]methanesulfonamide;hydron;chloride
• CAS: 88412-53-7
• 化学式: C₂₁H₂₀N₄O₂S*ClH
• 分子量: 428.942
• InChiKey: QUXLNGYUOXZRFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  91.5
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(methamine)-4-nitro-N-(methylsulfonyl)benzenamine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 N-[4-(acridin-9-ylamino)-3-(methylamino)phenyl]methanesulfonamide;hydron;chloride
  参考文献：
  名称：

  Potential antitumor agents. 48. 3'-Dimethylamino derivatives of amsacrine: redox chemistry and in vivo solid tumor activity

  摘要：

  Structure-activity relationships for a series of acridine-substituted 3'-N(CH3)2 derivatives of the clinical antileukemic drug amsacrine (1) are reported. The parent (unsubstituted) compound 3 has activity against the Lewis lung solid tumor that is superior to amsacrine (1), the new clinical amsacrine analogue 4, and the recently developed 3'-NHCH3 derivative 2. Although the compounds generally bind less well to DNA and are less dose potent in vivo than either their amsacrine (3'-OCH3) or 3'-NHCH3 analogues, they show very high levels of antitumor activity, with the 4-OCH3 derivative capable of effecting 100% cures of the Lewis lung solid tumor. The broad structure-activity relationships for acridine substitution more closely resemble those of the amsacrine than the 3'-NHCH3 series, with 4-substituted and 4,5-disubstituted compounds showing the highest activity.

  DOI：

  10.1021/jm00387a012