3',4'-didemethylepipodophyllotoxin | 102306-97-8

• 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: 3',4'-didemethylepipodophyllotoxin
• 英文别名: (5S,5aR,8aR,9R)-9-(3,4-dihydroxy-5-methoxyphenyl)-5-hydroxy-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• CAS: 102306-97-8
• 化学式: C₂₀H₁₈O₈
• 分子量: 386.358
• InChiKey: UCILNJOMIKDJGF-HQKIHSOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  鬼臼毒素 在 甲烷磺酸 、 二甲基硫 、 三氟乙酸 作用下， 反应 9.0h， 以1.1 g的产率得到3',4'-didemethylepipodophyllotoxin
  参考文献：
  名称：

  Practical Demethylation of Podophyllotoxin and Efficient Preparation of 4-Amino-4-deoxy-4′-demethylepipodophyllotoxin

  摘要：

  4'-Demethylepipodophyllotoxin (4'-DMEP) was readily available through demethylation of podophyllotoxin using methionine in methanesulfonic acid in the presence of TFA (or acetone/water). Thus, 4-amino-4-deoxy-4'-demethylepipodophyllotoxin was obtained in three steps in excellent yield by a Ritter reaction on 4'-DMEP, followed by treatment with thiourea in AcOH.

  DOI：

  10.1080/00397911.2011.567436

文献信息

• Antitumor agents. 78. Inhibition of human DNA topoisomerase II by podophyllotoxin and .alpha.-peltatin analogs
  作者：Lee S. Thurston、Hiroshi Irie、Shohei Tani、Fu Sheng Han、Zong Chao Liu、Yung Chi Cheng、Kuo Hsiung Lee

  DOI：10.1021/jm00158a042

  日期：1986.8

  It has been reported that the action of etoposide (VP-16) (14) as an antitumor agent is mediated through its interaction with DNA topoisomerase II which results in DNA breakage inside the cell. In order to understand the mechanism of action as well as structure-activity relationships of 14, several novel, synthetic and some naturally occurring analogues related to podophyllotoxin were examined for inhibition of the DNA topoisomerase II activity. Compound 2 exhibited enhanced activity and compound 5 slightly diminished activity relative to 14. A 4 beta-substituted ether at the C ring and O-demethylation at the E ring appear to enhance activity.
• [EN] COMBINATION THERAPY UTILIZING DNA ALKYLATING AGENTS AND ATR INHIBITORS<br/>[FR] POLYTHÉRAPIE UTILISANT DES AGENTS D'ALKYLATION D'ADN ET DES INHIBITEURS D'ATR
  申请人：MERCK PATENT GMBH

  公开号：WO2020078905A1

  公开（公告）日：2020-04-23

  The present invention relates to synergistic combinations of DNA-alkylating ADCs and ATR inhibitors.