7-((N-(2-hydroxyethyl)amino)methyl)-(20S)-camptothecin | 1622254-80-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 英文名称: 7-((N-(2-hydroxyethyl)amino)methyl)-(20S)-camptothecin
• 英文别名: (19S)-19-ethyl-19-hydroxy-10-[(2-hydroxyethylamino)methyl]-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione
• CAS: 1622254-80-1
• 化学式: C₂₃H₂₃N₃O₅
• 分子量: 421.453
• InChiKey: CUJYFSDHNIINTP-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  喜树碱 在 硫酸 、 双氧水 、 iron(II) sulfate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 7-((N-(2-hydroxyethyl)amino)methyl)-(20S)-camptothecin
  参考文献：
  名称：

  Design and synthesis of new 7-(N-substituted-methyl)-camptothecin derivatives as potent cytotoxic agents

  摘要：

  A series of novel 7-(N-substituted-methyl)-camptothecin derivatives was designed, synthesized, and evaluated for in vitro cytotoxicity against four human tumor cell lines, A-549, MDA-MB-231, KB, and KBvin. All of the derivatives showed promising in vitro cytotoxic activity against the tested tumor cell lines, with IC50 values ranging from 0.0023 to 1.11 μM, and were as or more potent than topotecan. Compounds 9d, 9e, and 9r exhibited the highest antiproliferative activity among all prepared derivatives. Furthermore, all of the compounds were more potent than paclitaxel against the multidrug-resistant (MDR) KBvin subline. With a concise efficient synthesis and potent cytotoxic profiles, especially significant activity towards KBvin, compounds 9d, 9e, and 9r merit further development as a new generation of camptothecin-derived anticancer clinical trial candidates.

  DOI：

  10.1016/j.bmcl.2014.06.060