20(S)-O-triethylsilylcamptothecin | 1004264-93-0

• 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(S)-O-triethylsilylcamptothecin
• 英文别名: 20-OTES-camptothecin；(19S)-19-ethyl-19-triethylsilyloxy-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: 1004264-93-0
• 化学式: C₂₆H₃₀N₂O₄Si
• 分子量: 462.621
• InChiKey: NDPQESGITFHDPN-SANMLTNESA-N

物化性质

• 沸点：
  691.7±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  20(S)-O-triethylsilylcamptothecin 在 N-氟代双苯磺酰胺 、 triethylamine tris(hydrogen fluoride) 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 33.33h， 生成 20-OH-5-fluorocamptothecin
  参考文献：
  名称：

  WO2008/12003

  摘要：

  公开号：
• 作为产物：
  描述：

  三乙基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 46.17h， 生成 20(S)-O-triethylsilylcamptothecin
  参考文献：
  名称：

  WO2008/11992

  摘要：

  公开号：

文献信息

• CAMPTOTHECIN DERIVATIVES WITH ANTITUMOR ACTIVITY
  申请人：Fontana Gabriele

  公开号：US20100063082A1

  公开（公告）日：2010-03-11

  Novel camptothecin derivatives having antitumor activity, the processes for the preparation thereof, the use thereof as antitumor drugs and pharmaceutical compositions containing them.

  具有抗肿瘤活性的新型紫杉醇衍生物，其制备方法，作为抗肿瘤药物的用途以及含有它们的药物组合物。
• Semisynthesis, Biological Activity, and Molecular Modeling Studies of C-Ring-Modified Camptothecins
  作者：Cristian Samorì、Andrea Guerrini、Greta Varchi、Gabriele Fontana、Ezio Bombardelli、Stella Tinelli、Giovanni Luca Beretta、Serena Basili、Stefano Moro、Franco Zunino、Arturo Battaglia

  DOI：10.1021/jm801153y

  日期：2009.2.26

  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.
• Thiocamptothecin
  作者：Cristian Samorì、Andrea Guerrini、Greta Varchi、Franco Zunino、Giovanni Luca Beretta、Cristina Femoni、Ezio Bombardelli、Gabriele Fontana、Arturo Battaglia

  DOI：10.1021/jm8001982

  日期：2008.5.1

  The synthesis and the X-ray structure of 16a-thiocamptothecin (TCPT), the thiopyridone analog of camptothecin (CPT), are accomplished. The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Methylation of TCPT leads to the cleavage of the C-ring. The cytotoxic activity of TCPT was evaluated against different human tumor cell lines using CPT as reference compound.
• WO2008/11994
  申请人：——

  公开号：——

  公开（公告）日：——