4-β-(benzenesulphonyl)amino 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: 4-β-(benzenesulphonyl)amino podophyllotoxin
• 英文别名: N-[(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]benzenesulfonamide
• 化学式: C₂₈H₂₇NO₉S
• 分子量: 553.59
• InChiKey: QXGBGOGXIAKENE-QNMIOERPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  鬼臼毒素 在 palladium on activated charcoal sodium azide 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 4-β-(benzenesulphonyl)amino podophyllotoxin
  参考文献：
  名称：

  Synthesis of 4β-amido and 4β-sulphonamido analogues of podophyllotoxin as potential antitumour agents

  摘要：

  The new 4beta-amido analogues of podophyllotoxin or 4'-O-demethylepipodophyllotoxin have been prepared either by the coupling of 4beta-amino podophyllotoxin or 4beta-amino-4'-O-demethyl epipodophyllotoxin with the corresponding acids in presence of DCC in dichloromethane or by treating the appropriate acid chloride or sulphonyl chloride in presence of Et3N. These 4beta-amido and 4beta-sulphonamido derivatives of podophyllotoxin have been evaluated for their cytotoxicity against six human cancer cell lines. Some of these analogues have shown promising anticancer activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.019

文献信息

• Natural Products-Based Insecticidal Agents 1. Semisynthesis and Insecticidal Activity of 4β-Benzenesulfonamide Derivatives of Podophyllotoxin against Mythimna separata Walker
  作者：Hui Xu、Lei Zhang、Bao-Feng Su、Xing Zhang、Xuan Tian

  DOI：10.3987/com-08-s(f)14

  日期：——

  Eleven 4 beta-benzenesulfonamide derivatives of podophyllotoxin were synthesized and evaluated for insecticidal activity against the third-instar larvae of Mythimna separata Walker in vivo at the concentration of 1 mg/mL. All derivatives showed delayed insecticidal activity, which was different from the traditional neurotoxic insecticides. Compounds 4a-4f and 4i-4k were found to be more potent than podopyllotoxin in the mortality rate after 20 d against M separata. Especially compounds 4i, the corresponding final mortality rate of which was 88.9%, exhibited more potent insecticidal activity than toosendandin (81.4%), a commercial insecticide derived from Melia azedarach. Furthermore, some preliminary qualitative structure-activity relationships were also observed.
• Synthesis of 4β-amido and 4β-sulphonamido analogues of podophyllotoxin as potential antitumour agents
  作者：Ahmed Kamal、B Ashwini Kumar、M Arifuddin、Sunanda G Dastidar

  DOI：10.1016/j.bmc.2003.08.019

  日期：2003.11

  The new 4beta-amido analogues of podophyllotoxin or 4'-O-demethylepipodophyllotoxin have been prepared either by the coupling of 4beta-amino podophyllotoxin or 4beta-amino-4'-O-demethyl epipodophyllotoxin with the corresponding acids in presence of DCC in dichloromethane or by treating the appropriate acid chloride or sulphonyl chloride in presence of Et3N. These 4beta-amido and 4beta-sulphonamido derivatives of podophyllotoxin have been evaluated for their cytotoxicity against six human cancer cell lines. Some of these analogues have shown promising anticancer activity. (C) 2003 Elsevier Ltd. All rights reserved.