4'-demethyl-1-O-[4,6-O-(4-azido-5-iodo-2-methoxybenzylidene)-β-D-glucopyranosyl]epipodophyllotoxin | 367927-11-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 4'-demethyl-1-O-[4,6-O-(4-azido-5-iodo-2-methoxybenzylidene)-β-D-glucopyranosyl]epipodophyllotoxin
• CAS: 367927-11-5
• 化学式: C₃₅H₃₄IN₃O₁₄
• 分子量: 847.571
• InChiKey: GYUHMDBICRQJMU-VEJVCMFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  53.0
• 可旋转键数：
  8.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  218.82
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  4-氨基水杨酸 在 chromium(VI) oxide 、 sodium azide 、 硫酸 、 chloroamine-T 、 二异丁基氢化铝 、 potassium carbonate 、 对甲苯磺酸 、 sodium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醚 、 硝基甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 56.75h， 生成 4'-demethyl-1-O-[4,6-O-(4-azido-5-iodo-2-methoxybenzylidene)-β-D-glucopyranosyl]epipodophyllotoxin
  参考文献：
  名称：

  Synthesis and Biological Activity of a Photoaffinity Etoposide Probe

  摘要：

  The epipodophyllotoxin etoposide is a potent and widely used anticancer drug that targets DNA topoisomerase II. The synthesis, photochemical, and biological testing of a photoactivatable aromatic azido analogue of etoposide also containing an iodo group is described. This azido analogue should prove useful for identifying the etoposide interaction site on topoisomerase II, Irradiation of the azido analogue and an aldehyde-conntaining azido precursor with UV light produced changes in their UV-visible spectra that were consistent with photoactivation. The azido analogue strongly inhibited topoisomerase II and inhibited the growth of Chinese Hamster Ovary cells. Azido analogue-induced topoisomerase II-DNA covalent complexes were significantly increased subsequent to UV irradiation of drug-treated human leukemia K562 calls as compared to etoposide-treated cells. These results suggest that the photoactivated form of etoposide is a more effective topoisomerase II poison either by interacting directly with the enzyme or with DNA subsequent to topoisnmerase II-mediated strand cleavage. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00102-x