4β-(N-[4-[2-(diisopropylamino)ethyl]phenyl]amino)-4'-O-demethyl-4-desoxypodophyllotoxin

• 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: 4β-(N-[4-[2-(diisopropylamino)ethyl]phenyl]amino)-4'-O-demethyl-4-desoxypodophyllotoxin
• 英文别名: (5S,5aS,8aR,9R)-5-[4-[2-[di(propan-2-yl)amino]ethyl]anilino]-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• 化学式: C₃₆H₄₄N₂O₇
• 分子量: 616.755
• InChiKey: BAZDIOPAHROREN-BJHVCKBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  87.7
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,2-dibromo-1-(4-nitrophenyl)ethene 在 sodium tetrahydroborate 、 10% palladium on activated charcoal 、 三氟化硼乙醚 、 水 、 氢气 、 三乙胺 、 barium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 生成 4β-(N-[4-[2-(diisopropylamino)ethyl]phenyl]amino)-4'-O-demethyl-4-desoxypodophyllotoxin
  参考文献：
  名称：

  Synthesis and biological evaluation of new 4β-anilino-4′-O-demethyl-4-desoxypodophyllotoxin derivatives as potential antitumor agents

  摘要：

  A series of new 4 beta-anilino-4'-O-demethyl-4-desoxypodophyllotoxin derivatives were prepared and evaluated for their cytotoxicities against four human cancer cell lines including KB, KB/VCR, A549 and 95D. Most compounds showed better growth-inhibition activities against tested cell lines than that of etoposide (VP-16). Preliminary structure-activity relationships (SARs) were concluded and it indicated that the side chains substituted at 4 beta position of podophyllotoxin significantly influenced the cytotoxic activity, especially for the drug resistance profile. In vivo studies of compound 26c on highly metastatic human lung cancer xenograft in nude mice showed that it can significantly inhibit tumor growth with administrating by oral route. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.016

文献信息

• Synthesis and biological evaluation of new 4β-anilino-4′-O-demethyl-4-desoxypodophyllotoxin derivatives as potential antitumor agents
  作者：Li Wang、Fenyan Yang、Xiaochun Yang、Xianghong Guan、Chunqi Hu、Tao Liu、Qiaojun He、Bo Yang、Yongzhou Hu

  DOI：10.1016/j.ejmech.2010.11.016

  日期：2011.1

  A series of new 4 beta-anilino-4'-O-demethyl-4-desoxypodophyllotoxin derivatives were prepared and evaluated for their cytotoxicities against four human cancer cell lines including KB, KB/VCR, A549 and 95D. Most compounds showed better growth-inhibition activities against tested cell lines than that of etoposide (VP-16). Preliminary structure-activity relationships (SARs) were concluded and it indicated that the side chains substituted at 4 beta position of podophyllotoxin significantly influenced the cytotoxic activity, especially for the drug resistance profile. In vivo studies of compound 26c on highly metastatic human lung cancer xenograft in nude mice showed that it can significantly inhibit tumor growth with administrating by oral route. (C) 2010 Elsevier Masson SAS. All rights reserved.