4'-O-demethyl-2'-chloro-4β-(3"-hydroxyanilino)-4-desoxypodophyllotoxin | 138261-35-5

• 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: 4'-O-demethyl-2'-chloro-4β-(3"-hydroxyanilino)-4-desoxypodophyllotoxin
• 英文别名: (5S-(5alpha,5abeta,8aalpha,9beta))-5-(2-Chloro-4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-9-((3-hydroxyphenyl)amino)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one；(5S,5aS,8aR,9S)-9-(2-chloro-4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxyanilino)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• CAS: 138261-35-5
• 化学式: C₂₇H₂₄ClNO₈
• 分子量: 525.942
• InChiKey: PIJSUFSQZFVNPL-WLZNGNGHSA-N

物化性质

• 沸点：
  741.4±60.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2'-chloro-4'-demethylpodophyllotoxin 在 氢溴酸 、 barium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 1.5h， 生成 4'-O-demethyl-2'-chloro-4β-(3"-hydroxyanilino)-4-desoxypodophyllotoxin
  参考文献：
  名称：

  Antitumor agents. 123. Synthesis and human DNA topoisomerase II inhibitory activity of 2'-chloro derivatives of etoposide and 4.beta.-(arylamino)-4'-O-demethylpodophyllotoxins

  摘要：

  The 2'-chloro derivatives of etoposide and 4-beta-(arylamino)-4'-O-demethylpodophyllotoxins 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. The results showed that none of the compounds are active as a result of the C-2' chloro substitution on ring E. This would suggest that the free rotation of ring E is essential for the aforementioned enzyme inhibitory activity. In addition, these 2'-chloro derivatives showed no significant cytotoxicity (KB).

  DOI：

  10.1021/jm00083a009