N-[4-[(4,5-dimethylacridin-9-yl)amino]-3-(dimethylamino)phenyl]methanesulfonamide;hydrochloride | 88913-85-3

• 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-[(4,5-dimethylacridin-9-yl)amino]-3-(dimethylamino)phenyl]methanesulfonamide;hydrochloride
• CAS: 88913-85-3
• 化学式: C₂₄H₂₆N₄O₂S*ClH
• 分子量: 471.023
• InChiKey: AJLRDLNCJFQERN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.33
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N,N-Dimethyl-2-Nitro-5-Aminoaniline 在 palladium on activated charcoal 吡啶 、 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、202.65 kPa 条件下， 反应 4.25h， 生成 N-[4-[(4,5-dimethylacridin-9-yl)amino]-3-(dimethylamino)phenyl]methanesulfonamide;hydrochloride
  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