4'-demethyl-4-deoxypodophyllotoxin 4'-(4-p-fluorophenylpiperazine) carbamate | 1308813-82-2

• 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-4-deoxypodophyllotoxin 4'-(4-p-fluorophenylpiperazine) carbamate
• 英文别名: [4-[(5R,5aR,8aR)-6-oxo-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-5-yl]-2,6-dimethoxyphenyl] 4-(4-fluorophenyl)piperazine-1-carboxylate
• CAS: 1308813-82-2
• 化学式: C₃₂H₃₁FN₂O₈
• 分子量: 590.605
• InChiKey: GAPOJWVJDIQLPX-MXXBPKCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  去氧鬼臼毒素 在 吡啶 、 甲烷磺酸 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 4'-demethyl-4-deoxypodophyllotoxin 4'-(4-p-fluorophenylpiperazine) carbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of derivatives of 4-deoxypodophyllotoxin as antitumor agents

  摘要：

  In an attempt to generate compounds with superior bioactivity and reduced toxicity, a series of derivatives of deoxypodophyllotoxin were synthesized by reacting 4'-demethyl-4-deoxypodophyllotoxin with substituted piperazines or their amino acid amides. The cytotoxic activity of these compounds against three human cancer cell lines was evaluated. We found that p-nitrophenylpiperazine substitution (Compound 8b) led to an increase in the potency of the compound. Compound 8b exhibited the most potent cytotoxicity against A-549, HeLa and SiHa cells (IC50 values were 0.102, 0.180 and 0.0195 mu M, respectively). In addition, flow cytometric analysis showed that 8b induced cell cycle arrest in the G1 phase accompanied by apoptosis in A-549 cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.004

文献信息

• Synthesis and biological evaluation of derivatives of 4-deoxypodophyllotoxin as antitumor agents
  作者：Yan Jin、Jie Liu、Wen-Ting Huang、Shi-Wu Chen、Ling Hui

  DOI：10.1016/j.ejmech.2011.06.004

  日期：2011.9

  In an attempt to generate compounds with superior bioactivity and reduced toxicity, a series of derivatives of deoxypodophyllotoxin were synthesized by reacting 4'-demethyl-4-deoxypodophyllotoxin with substituted piperazines or their amino acid amides. The cytotoxic activity of these compounds against three human cancer cell lines was evaluated. We found that p-nitrophenylpiperazine substitution (Compound 8b) led to an increase in the potency of the compound. Compound 8b exhibited the most potent cytotoxicity against A-549, HeLa and SiHa cells (IC50 values were 0.102, 0.180 and 0.0195 mu M, respectively). In addition, flow cytometric analysis showed that 8b induced cell cycle arrest in the G1 phase accompanied by apoptosis in A-549 cells. (C) 2011 Elsevier Masson SAS. All rights reserved.