4β-(5-methoxycarbonyl-1,2,3-triazole)-podophyllotoxin | 1203582-82-4

• 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: 4β-(5-methoxycarbonyl-1,2,3-triazole)-podophyllotoxin
• 英文别名: methyl 3-[(5S,5aS,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]triazole-4-carboxylate
• CAS: 1203582-82-4
• 化学式: C₂₆H₂₅N₃O₉
• 分子量: 523.499
• InChiKey: KNESDOQFHILTIZ-RNAPXVLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  丙炔酸甲酯 、 4β-azido-4-deoxypodophyllotoxin 以 乙醇 为溶剂， 反应 8.0h， 以30%的产率得到4β-(4-carbomethoxy-1,2,3-triazolyl)epipodophyllotoxin
  参考文献：
  名称：

  Synthesis of 4β-triazole-podophyllotoxin derivatives by azide–alkyne cycloaddition and biological evaluation as potential antitumor agents

  摘要：

  A representative synthetic process of derivatizing the natural product podophyllotoxin utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) is described including molecular design, reaction optimization and X-ray structure confirmation. Evaluation of cytotoxicity against human cancer cell lines (Hela, K562 and K562/A02) using MTT assay proves that these triazole derivatives have good antitumor activities. High activities toward the drug resistant K562/A02 cell line reveal promising future for these derivatives. The rarely prepared 1,5-disubstituted triazole isomers, which would be omitted by the "click chemistry", were found to have superior cytotoxicities to that of the 1,4-disubstituted isomers. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.024

文献信息

• Synthesis of 4β-triazole-podophyllotoxin derivatives by azide–alkyne cycloaddition and biological evaluation as potential antitumor agents
  作者：Hong Chen、Song Zuo、Xiaochen Wang、Xiaowei Tang、Ming Zhao、Yanling Lu、Liting Chen、Jing Liu、Yongfeng Liu、Dailin Liu、Shi Zhang、Tan Li

  DOI：10.1016/j.ejmech.2011.07.024

  日期：2011.9

  A representative synthetic process of derivatizing the natural product podophyllotoxin utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) is described including molecular design, reaction optimization and X-ray structure confirmation. Evaluation of cytotoxicity against human cancer cell lines (Hela, K562 and K562/A02) using MTT assay proves that these triazole derivatives have good antitumor activities. High activities toward the drug resistant K562/A02 cell line reveal promising future for these derivatives. The rarely prepared 1,5-disubstituted triazole isomers, which would be omitted by the "click chemistry", were found to have superior cytotoxicities to that of the 1,4-disubstituted isomers. (C) 2011 Elsevier Masson SAS. All rights reserved.