20-OH-5-(3-hydroxypropyl)camptothecin | 1350008-59-1

• 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: 20-OH-5-(3-hydroxypropyl)camptothecin
• 英文别名: (19S)-19-ethyl-19-hydroxy-12-(3-hydroxypropyl)-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: 1350008-59-1
• 化学式: C₂₃H₂₂N₂O₅
• 分子量: 406.438
• InChiKey: KEVVFCNVDXPVBE-IMMUGOHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (19S)-12-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-19-ethyl-19-hydroxy-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 在 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到20-OH-5-(3-hydroxypropyl)camptothecin
  参考文献：
  名称：

  Semisynthesis, Biological Activity, and Molecular Modeling Studies of C-Ring-Modified Camptothecins

  摘要：

  The synthesis, biological activity, and molecular modeling studies of C-ring-rnodified camptothecins are reported. A general synthetic protocol, based on "C-5 camptothecin (C-5-CPT) enolate chemistry", allows one to obtain various C5-substituted analogues. All new Compounds, obtained as 1:1 epimeric mixtures, were tested for their antiproliferative activity. Experimental data showed that all novel derivatives are less active than the reference compounds and that one of the two epimers; is more active than the other. Molecular docking simulations were performed to achieve more insight into the interactions between the new C5-modified CPTs and Topo I. A good correlation was observed when the data of cytotoxicity and the values calculated for the free binding energy were combined.

  DOI：

  10.1021/jm801153y