4β-(2"-hydroxyanilino)-4-desoxypodophyllotoxin | 125830-28-6

• 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-(2"-hydroxyanilino)-4-desoxypodophyllotoxin
• 英文别名: (5S,5aS,8aR,9R)-5-(2-hydroxyanilino)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• CAS: 125830-28-6
• 化学式: C₂₈H₂₇NO₈
• 分子量: 505.524
• InChiKey: DQJBUVJFBGCGSL-JHOAZWNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  鬼臼毒素 在 甲烷磺酸 、 barium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 11.25h， 生成 4β-(2"-hydroxyanilino)-4-desoxypodophyllotoxin
  参考文献：
  名称：

  Facile and efficient one-pot synthesis of 4β-arylaminopodophyllotoxins: synthesis of DNA topoisomerase II inhibitors (NPF and W-68)

  摘要：

  A series of 4 beta-arylamino-4'-O-demethylepipodophyllotoxins and 4 beta-arylaminoepipodophyllotoxins have been synthesized with significant stereoselectivity and improved yields by employing the methanesulphonic acid/sodium iodide reagent system. Compounds NPF, W-68 and other DNA topoisomerase II inhibitors are prepared in good to excellent yields by this method and these are active or more active than etoposide in their inhibition of the human DNA topoisomerase II. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00407-8

文献信息

• Antitumor agents. 111. New 4-hydroxylated and 4-halogenated anilino derivatives of 4'-demethylepipodophyllotoxin as potent inhibitors of human DNA topoisomerase II
  作者：Kuo Hsiung Lee、Scott A. Beers、Masami Mori、Zhe Qing Wang、Yao Haur Kuo、Li Li、Su Ying Liu、Jang Yang Chang、Fu Sheng Han、Yung Chi Cheng

  DOI：10.1021/jm00167a013

  日期：1990.5

  A series of C-4 hydroxylated and halogenated anilino derivatives of epipodophyllotoxin or 4'-demethylepipodophyllotoxin have been synthesized and evaluated for their inhibitory activity against the human DNA topoisomerase II as well as for their activity in causing cellular protein-linked DNA breakage. Compounds 11-17 and 22 are more potent than etoposide in causing DNA breakage, while compounds 11-13, 15, 16, and 20 are as active or more active than etoposide in their inhibition of the human DNA topoisomerase II. The cytotoxicity in KB cells appears to have no direct correlation with their ability to inhibit DNA topoisomerase II and to cause protein-linked DNA breaks in cells.
• LEE, KUO-HSIUNG;BEERS, SCOTT A.;MORI, MASAMI;WANG, ZHE-QING;KUO, YAO-HAUR+, J. MED. CHEM., 33,(1990) N, C. 1364-1368
  作者：LEE, KUO-HSIUNG、BEERS, SCOTT A.、MORI, MASAMI、WANG, ZHE-QING、KUO, YAO-HAUR+

  DOI：——

  日期：——
• Facile and efficient one-pot synthesis of 4β-arylaminopodophyllotoxins: synthesis of DNA topoisomerase II inhibitors (NPF and W-68)
  作者：Ahmed Kamal、N. Laxman、G. Ramesh

  DOI：10.1016/s0960-894x(00)00407-8

  日期：2000.9

  A series of 4 beta-arylamino-4'-O-demethylepipodophyllotoxins and 4 beta-arylaminoepipodophyllotoxins have been synthesized with significant stereoselectivity and improved yields by employing the methanesulphonic acid/sodium iodide reagent system. Compounds NPF, W-68 and other DNA topoisomerase II inhibitors are prepared in good to excellent yields by this method and these are active or more active than etoposide in their inhibition of the human DNA topoisomerase II. (C) 2000 Elsevier Science Ltd. All rights reserved.