4'-O-demethyl-4β-[(4-hydroxymethyl)-1,2,3-triazol-1-yl]-4-desoxypodophyllotoxin morpholino carbamate | 1443920-19-1

• 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'-O-demethyl-4β-[(4-hydroxymethyl)-1,2,3-triazol-1-yl]-4-desoxypodophyllotoxin morpholino carbamate
• 英文别名: [1-[(5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]triazol-4-yl]methyl morpholine-4-carboxylate
• CAS: 1443920-19-1
• 化学式: C₂₉H₃₀N₄O₁₀
• 分子量: 594.578
• InChiKey: LTSAKYBFLAWTOD-QNMIOERPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  4'-去甲基表鬼臼毒素 在 吡啶 、 4-二甲氨基吡啶 、 copper(ll) sulfate pentahydrate 、 三氟化硼乙醚 、 氨 、 sodium ascorbate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 10.75h， 生成 4'-O-demethyl-4β-[(4-hydroxymethyl)-1,2,3-triazol-1-yl]-4-desoxypodophyllotoxin morpholino carbamate
  参考文献：
  名称：

  Synthesis and cytotoxic activity on human cancer cells of carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin

  摘要：

  Carbamate derivatives of 4 beta-(1,2,3-triazol-1-yl)podophyllotoxin were synthesized by means of click chemistry, and their cytotoxicities against human cancer cell lines HL-60, A-549, HeLa, and HCT-8 were evaluated. Some compounds were more potent than the anticancer drug etoposide. 4'-O-Demethyl-4 beta-[(4-hydroxymethyl)-1,2,3-triazol-1-yl]-4-deoxypodophyllotoxin cyclopentyl carbamate, the most potent compound, induced cell cycle arrest in the G2/M phase accompanied by apoptosis in A-549 cells. Furthermore, this compound inhibited the formation of microtubules in A-549 cells and caused the inhibition of DNA topoisomerase-II. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.068

文献信息

• Synthesis and cytotoxic activity on human cancer cells of carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin
  作者：Jian-Fei Liu、Chun-Yan Sang、Xiao-Hui Xu、Lin-Lin Zhang、Xuan Yang、Lin Hui、Jin-Bang Zhang、Shi-Wu Chen

  DOI：10.1016/j.ejmech.2013.03.068

  日期：2013.6

  Carbamate derivatives of 4 beta-(1,2,3-triazol-1-yl)podophyllotoxin were synthesized by means of click chemistry, and their cytotoxicities against human cancer cell lines HL-60, A-549, HeLa, and HCT-8 were evaluated. Some compounds were more potent than the anticancer drug etoposide. 4'-O-Demethyl-4 beta-[(4-hydroxymethyl)-1,2,3-triazol-1-yl]-4-deoxypodophyllotoxin cyclopentyl carbamate, the most potent compound, induced cell cycle arrest in the G2/M phase accompanied by apoptosis in A-549 cells. Furthermore, this compound inhibited the formation of microtubules in A-549 cells and caused the inhibition of DNA topoisomerase-II. (C) 2013 Elsevier Masson SAS. All rights reserved.