N-[4-(acridin-9-ylamino)-3-(methylamino)phenyl]pentane-1-sulfonamide | 88412-81-1

• 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]pentane-1-sulfonamide
• CAS: 88412-81-1
• 化学式: C₂₅H₂₈N₄O₂S
• 分子量: 448.589
• InChiKey: LEXFOKPQTAXAPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  91.5
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  戊烷-1-磺酰氯 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.25h， 生成 N-[4-(acridin-9-ylamino)-3-(methylamino)phenyl]pentane-1-sulfonamide
  参考文献：
  名称：

  Potential antitumor agents. 41. Analogs of amsacrine with electron-donor substituents in the anilino ring

  摘要：

  The preparation and antitumor activity of a series of 3'-alkylamino and 3'-dialkylamino analogues of amsacrine are reported. The results support previous work suggesting that the presence of electron-donating groups in the 3'-position of the anilino ring substantially enhance the antitumor activity of amsacrine analogues, possibly by the provision of high levels of electron density at the 6'-position. The alkylamino derivatives generally possess tighter DNA binding, higher levels of in vitro and in vivo antileukemic activity, and greater aqueous solubility than the corresponding amsacrine analogues.

  DOI：

  10.1021/jm00369a022

文献信息

• Potential antitumor agents. 41. Analogs of amsacrine with electron-donor substituents in the anilino ring
  作者：Graham J. Atwell、Gordon W. Rewcastle、William A. Denny、Bruce F. Cain、Bruce C. Baguley

  DOI：10.1021/jm00369a022

  日期：1984.3

  The preparation and antitumor activity of a series of 3'-alkylamino and 3'-dialkylamino analogues of amsacrine are reported. The results support previous work suggesting that the presence of electron-donating groups in the 3'-position of the anilino ring substantially enhance the antitumor activity of amsacrine analogues, possibly by the provision of high levels of electron density at the 6'-position. The alkylamino derivatives generally possess tighter DNA binding, higher levels of in vitro and in vivo antileukemic activity, and greater aqueous solubility than the corresponding amsacrine analogues.