4'-O-all-cis-5,8,11,14-eicosatetraenoyl-4'-demethyldeoxypodophyllotoxin

• 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-all-cis-5,8,11,14-eicosatetraenoyl-4'-demethyldeoxypodophyllotoxin
• 英文别名: 4'-O-arachidonyl-4'-demethyldeoxypodophyllotoxin；[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] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
• 化学式: C₄₁H₅₀O₈
• 分子量: 670.843
• InChiKey: IYTYSJISGKMYLX-PGHHDLJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  49
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  去氧鬼臼毒素 在 4-二甲氨基吡啶 、 碘代三甲硅烷 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 4'-O-all-cis-5,8,11,14-eicosatetraenoyl-4'-demethyldeoxypodophyllotoxin
  参考文献：
  名称：

  Antitumor activity of unsaturated fatty acid esters of 4′-demethyldeoxypodophyllotoxin

  摘要：

  Unsaturated fatty acid esters of 4-demethyldeoxypodophyllotoxin (DDPT) were prepared and tested for antitumor activity. The esters showed increased in vivo antitumor activity despite the lower in vitro activity than DDPT. Especially, the ester (DFE12) of all-cis-11,14-eicosadienoic acid was much better (IR, 83%) than VP-16 (IR, 60%) without loss of body weight. Unsaturated fatty acids could be evaluated to be good carrier vehicles of DDPT. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00558-4

文献信息

• Antitumor activity of unsaturated fatty acid esters of 4′-demethyldeoxypodophyllotoxin
  作者：Young-Jae You、Yong Kim、Nguyen-Hai Nam、Byung-Zun Ahn

  DOI：10.1016/s0960-894x(03)00558-4

  日期：2003.8

  Unsaturated fatty acid esters of 4-demethyldeoxypodophyllotoxin (DDPT) were prepared and tested for antitumor activity. The esters showed increased in vivo antitumor activity despite the lower in vitro activity than DDPT. Especially, the ester (DFE12) of all-cis-11,14-eicosadienoic acid was much better (IR, 83%) than VP-16 (IR, 60%) without loss of body weight. Unsaturated fatty acids could be evaluated to be good carrier vehicles of DDPT. (C) 2003 Elsevier Ltd. All rights reserved.