(15S)-15-ethyl-15-hydroxy-17-oxa-10,21,22,23-tetrazahexacyclo[10.10.1.02,11.04,9.014,19.020,23]tricosa-2,4,6,8,10,12,14(19),20-octaen-16-one;2,2,2-trifluoroacetic acid | 1004264-56-5

• 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: (15S)-15-ethyl-15-hydroxy-17-oxa-10,21,22,23-tetrazahexacyclo[10.10.1.02,11.04,9.014,19.020,23]tricosa-2,4,6,8,10,12,14(19),20-octaen-16-one;2,2,2-trifluoroacetic acid
• CAS: 1004264-56-5
• 化学式: C₂HF₃O₂*C₂₀H₁₆N₄O₃
• 分子量: 474.396
• InChiKey: RXJOGCBMRSKUIO-FWCANSBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (15S)-15-ethyl-15-hydroxy-17-oxa-10,21,22,23-tetrazahexacyclo[10.10.1.02,11.04,9.014,19.020,23]tricosa-2,4,6,8,10,12,14(19),20-octaen-16-one;2,2,2-trifluoroacetic acid 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 以94%的产率得到triazole[5,4-c]16a-deoxocamptothecin
  参考文献：
  名称：

  CAMPTOTHECIN DERIVATIVES WITH ANTITUMOR ACTIVITY

  摘要：

  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。

  公开号：

  US20100063082A1
• 作为产物：
  描述：

  20-OTES-5DTBAC-CPT 、 三氟乙酸 以 1,2-dichloroethane (DCE) 为溶剂， 反应 24.0h， 以55%的产率得到(15S)-15-ethyl-15-hydroxy-17-oxa-10,21,22,23-tetrazahexacyclo[10.10.1.02,11.04,9.014,19.020,23]tricosa-2,4,6,8,10,12,14(19),20-octaen-16-one;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  CAMPTOTHECIN DERIVATIVES WITH ANTITUMOR ACTIVITY

  摘要：

  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。

  公开号：

  US20100063082A1

文献信息

• 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.