4'-O-demethyl-2'-chloro-4β-(4"-chloroanilino)-4-desoxypodophyllotoxin | 138261-39-9

• 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-(4"-chloroanilino)-4-desoxypodophyllotoxin
• 英文别名: (5S,5aS,8aR,9S)-5-(4-chloroanilino)-9-(2-chloro-4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• CAS: 138261-39-9
• 化学式: C₂₇H₂₃Cl₂NO₇
• 分子量: 544.388
• InChiKey: IOJAJDWZXZTPMW-WLZNGNGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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：
  95.5
• 氢给体数：
  2
• 氢受体数：
  8

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-(4"-chloroanilino)-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

文献信息

• Antitumor agents. 123. Synthesis and human DNA topoisomerase II inhibitory activity of 2'-chloro derivatives of etoposide and 4.beta.-(arylamino)-4'-O-demethylpodophyllotoxins
  作者：Hong Hu、Su Ying Liu、Yung Chi Cheng、Kuo Hsiung Lee、Zhe Qing Wang

  DOI：10.1021/jm00083a009

  日期：1992.3

  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).