methyl 4-azido-2-methoxy-5-iodobenzoate | 116519-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-azido-2-methoxy-5-iodobenzoate
• 英文别名: Methyl 4-azido-5-iodo-2-methoxybenzoate
• CAS: 116519-15-4
• 化学式: C₉H₈IN₃O₃
• 分子量: 333.085
• InChiKey: JPFMIWNHMWMQJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  84.29
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 4-azido-2-methoxy-5-iodobenzoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 4-azido-2-methoxy-5-iodobenzyl alcohol
  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
• 作为产物：
  描述：

  4-氨基水杨酸 在 sodium azide 、 硫酸 、 chloroamine-T 、 potassium carbonate 、 sodium iodide 、 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.0h， 生成 methyl 4-azido-2-methoxy-5-iodobenzoate
  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