hemisuccinic acid 4'-demethylepipodophyllotoxin-4-O-ester | 118356-09-5

• 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: hemisuccinic acid 4'-demethylepipodophyllotoxin-4-O-ester
• 英文别名: 4'-demethylepipodophyllotoxin 4-succinate；4-[[(5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]oxy]-4-oxobutanoic acid
• CAS: 118356-09-5
• 化学式: C₂₅H₂₄O₁₁
• 分子量: 500.459
• InChiKey: TWAAJRKTMQISEL-UTTLJGBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  二苄基磷酰基氯 、 hemisuccinic acid 4'-demethylepipodophyllotoxin-4-O-ester 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 、 甲苯 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Podophyllotoxin derivatives

  摘要：

  提供了Podophyllotoxin和4'-去甲基表皮Podophyllotoxin的4-O酯化物。这些化合物是Podophyllotoxin和4'-去甲基表皮Podophyllotoxin与烷基酸或取代烷基酸的4-O酯化物。这些化合物可用于治疗癌症。

  公开号：

  US20050004169A1
• 作为产物：
  描述：

  鬼臼毒素 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 水 、 氢溴酸 、 barium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 46.25h， 生成 hemisuccinic acid 4'-demethylepipodophyllotoxin-4-O-ester
  参考文献：
  名称：

  Antitumor agents. 100. Inhibition of human DNA topoisomerase II by cytotoxic ether and ester derivatives of podophyllotoxin and .alpha.-peltatin

  摘要：

  A principal mechanism of action of the clinical antitumor drugs etoposide (1) and teniposide (2) is the inhibition of catalytic activity of type II DNA topoisomerase and concurrent enzyme-mediated production of lethal DNA strand breaks. Substitution of the glycosidic moiety of 1 or 2 by ester and ethers, as well as the esterification and etherification of alpha-peltatin (4) including its glucosidic ethylidene and thenylidene cyclic acetals (25 and 26), has afforded compounds of much less activity than that of 1. The in vitro cytotoxicity (KB) appears to have no correlation with the inhibitory activity of the human DNA topoisomerase II.

  DOI：

  10.1021/jm00123a016

文献信息

• THURSTON, LEE S.;IMAKURA, YASUHIRO;HARUNA, MITSUMASA;LI, DE-HUA;LIU, ZONG+, J. MED. CHEM., 32,(1989) N, C. 604-608
  作者：THURSTON, LEE S.、IMAKURA, YASUHIRO、HARUNA, MITSUMASA、LI, DE-HUA、LIU, ZONG+

  DOI：——

  日期：——
• Antitumor agents. 100. Inhibition of human DNA topoisomerase II by cytotoxic ether and ester derivatives of podophyllotoxin and .alpha.-peltatin
  作者：Lee S. Thurston、Yasuhiro Imakura、Mitsumasa Haruna、De Hua Li、Zong Chao Liu、Su Ying Liu、Yung Chi Cheng、Kuo Hsiung Lee

  DOI：10.1021/jm00123a016

  日期：1989.3

  A principal mechanism of action of the clinical antitumor drugs etoposide (1) and teniposide (2) is the inhibition of catalytic activity of type II DNA topoisomerase and concurrent enzyme-mediated production of lethal DNA strand breaks. Substitution of the glycosidic moiety of 1 or 2 by ester and ethers, as well as the esterification and etherification of alpha-peltatin (4) including its glucosidic ethylidene and thenylidene cyclic acetals (25 and 26), has afforded compounds of much less activity than that of 1. The in vitro cytotoxicity (KB) appears to have no correlation with the inhibitory activity of the human DNA topoisomerase II.
• Podophyllotoxin derivatives
  申请人：Yang Li-Xi

  公开号：US20050004169A1

  公开（公告）日：2005-01-06

  4-O esters of podophyllotoxin and 4′-demethylepipodophyllotoxin are provided. The compounds are 4-O esters of an alkanoic acid or substituted alkanoic acid and podophyllotoxin and 4′-demethylepipodophyllotoxin. The compounds are useful for treating cancer.

  提供了Podophyllotoxin和4'-去甲基表皮Podophyllotoxin的4-O酯化物。这些化合物是Podophyllotoxin和4'-去甲基表皮Podophyllotoxin与烷基酸或取代烷基酸的4-O酯化物。这些化合物可用于治疗癌症。