4α-[(E)-3-phenyl-2-acrylate]-4-desoxy-podophyllotoxin

• 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: 4α-[(E)-3-phenyl-2-acrylate]-4-desoxy-podophyllotoxin
• 英文别名: [(5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] (E)-3-phenylprop-2-enoate
• 化学式: C₃₁H₂₈O₉
• 分子量: 544.558
• InChiKey: GRGPKFMGBKALPZ-VUBOJDGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  肉桂酸 、 鬼臼毒素 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以64%的产率得到4α-[(E)-3-phenyl-2-acrylate]-4-desoxy-podophyllotoxin
  参考文献：
  名称：

  Potential anti-MDR agents based on the podophyllotoxin scaffold: synthesis and antiproliferative activity evaluation against chronic myeloid leukemia cells by activating MAPK signaling pathways

  摘要：

  化合物9k在K562/ADR细胞中表现出优异的细胞毒性，诱导凋亡和G2/M细胞周期阻滞，下调Pgp表达并上调p-ERK1/2、p-JNK和p-p38的表达。

  DOI：

  10.1039/c5ra24272j

文献信息

• Synthesis and cytotoxicity of hydrophobic esters of podophyllotoxins
  作者：J.L. López-Pérez、E. del Olmo、B. de Pascual-Teresa、A. Abad、A. San Feliciano

  DOI：10.1016/j.bmcl.2003.12.039

  日期：2004.3

  Diverse norbornenecarboxylate esters of podophyllotoxin and its epimers and diastereoisomers have been prepared through Diels-Alder cycloaddition by treating the dienophilic acrylates of cyclolignans with cyclopentadiene. Their cytotoxicities against several cancer cell lines have been evaluated and the results compared with those found for other lignan esters. Podophyllotoxin adducts showed a one-fold increase in activity when compared to the natural product. The preparation of more hydrophobic esters, which showed less cytotoxicity, demonstrated that this activity is not primarily due to the lipophilic factor, but mainly to the spatial arrangement of the bulky moiety, which could contribute to increase the binding to the target site. (C) 2003 Elsevier Ltd. All rights reserved.
• Potential anti-MDR agents based on the podophyllotoxin scaffold: synthesis and antiproliferative activity evaluation against chronic myeloid leukemia cells by activating MAPK signaling pathways
  作者：Lei Zhang、Zeguo Zhang、Jing Wang、Yongzheng Chen、Fan Chen、Ya Lin、Xinling Zhu

  DOI：10.1039/c5ra24272j

  日期：——

  Compound 9k exhibited excellent cytotoxicity, induced apoptosis and G2/M cell cycle arrest, downregulated Pgp expression and up-regulated the expression of p-ERK1/2, p-JNK and p-p38 in K562/ADR cells.

  化合物9k在K562/ADR细胞中表现出优异的细胞毒性，诱导凋亡和G2/M细胞周期阻滞，下调Pgp表达并上调p-ERK1/2、p-JNK和p-p38的表达。