4-β-(4''-methylbenzophenone-2''-formyl)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-(4''-methylbenzophenone-2''-formyl)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[5,6-f][1,3]benzodioxol-5-yl]-2-benzoyl-5-methylbenzamide
• 化学式: C₃₇H₃₃NO₉
• 分子量: 635.67
• InChiKey: MDEFTRXTCYFEDD-NEVPTIFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  47
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  9

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 、 N,N'-二环己基碳二亚胺 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-(4''-methylbenzophenone-2''-formyl)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

• Podophyllotoxin derivatives as antitumor agents
  申请人：Kamal Ahmed

  公开号：US20070066837A1

  公开（公告）日：2007-03-22

  This invention relates to podophyllotoxin derivatives, more particularly to 4β-amino and 4β-amido derivatives of podophyllotoxin and 4′-O-demethylepipodophyllotoxin, which are useful for the treatment of tumors. Processes for the preparation of the compounds disclosed herein, pharmaceutical compositions containing these compounds, and methods for treating tumors are provided. The invention further relates to stereoselective compounds of podophyllotoxin and 4′-O-demethylepipodophyllotoxin derivatives.

  本发明涉及足叶草毒素衍生物，更具体地涉及4β-氨基和4β-酰胺衍生物以及4'-O-去甲基表儿茶素，这些衍生物对肿瘤的治疗有用。本发明提供了制备所述化合物的方法，含有这些化合物的制药组合物以及治疗肿瘤的方法。本发明还涉及足叶草毒素和4'-O-去甲基表儿茶素衍生物的立体选择性化合物。
• 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.