methyl 9-deoxy-9-oxo-α-apopicropodophyllate 9-n-hexylimine

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: methyl 9-deoxy-9-oxo-α-apopicropodophyllate 9-n-hexylimine
• 英文别名: methyl (7S,8R)-6-(hexyliminomethyl)-8-(3,4,5-trimethoxyphenyl)-7,8-dihydrobenzo[f][1,3]benzodioxole-7-carboxylate
• 化学式: C₂₉H₃₅NO₇
• 分子量: 509.599
• InChiKey: NJVFMSLUUXEVHG-KAYWLYCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  84.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  正己胺 、 methyl 9-deoxy-9-oxo-α-apopicropodophyllate 在 molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 336.0h， 以93%的产率得到methyl 9-deoxy-9-oxo-α-apopicropodophyllate 9-n-hexylimine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Selective Cytotoxic Cyclolignans Derived from Podophyllotoxin

  摘要：

  Podophyllotoxin and some of its derivatives are cyclolignans currently used for removing warts and in the clinical treatment of malign neoplasms. As such, they have been an objective of the scientific community for decades, in the search for more potent and more selective anticancer agents. Our interest in the chemoinduction of drug selectivity led us to the design and preparation of new podophyllotoxin derivatives by reaction of podophyllic aldehyde with aliphatic, aromatic, and heteroaromatic amines. Several of the resulting imines displayed a significant selectivity against human colon carcinoma cells, even higher than that of the starting aldehyde. Additional biological studies indicate that these derivatives induce microtubule depolymerization, arrest cells at the G(2)/M phase of cell cycle, and are able to induce a delayed apoptosis after 48 h of treatment, characterized by caspase-3 activation.

  DOI：

  10.1021/jm030978h

文献信息

• Synthesis and Biological Evaluation of New Selective Cytotoxic Cyclolignans Derived from Podophyllotoxin
  作者：María Angeles Castro、Jose María Miguel del Corral、Marina Gordaliza、Pablo A. García、María Antonia Gómez-Zurita、María Dolores García-Grávalos、Janis de la Iglesia-Vicente、Consuelo Gajate、Feiyun An、Faustino Mollinedo、Arturo San Feliciano

  DOI：10.1021/jm030978h

  日期：2004.2.1

  Podophyllotoxin and some of its derivatives are cyclolignans currently used for removing warts and in the clinical treatment of malign neoplasms. As such, they have been an objective of the scientific community for decades, in the search for more potent and more selective anticancer agents. Our interest in the chemoinduction of drug selectivity led us to the design and preparation of new podophyllotoxin derivatives by reaction of podophyllic aldehyde with aliphatic, aromatic, and heteroaromatic amines. Several of the resulting imines displayed a significant selectivity against human colon carcinoma cells, even higher than that of the starting aldehyde. Additional biological studies indicate that these derivatives induce microtubule depolymerization, arrest cells at the G(2)/M phase of cell cycle, and are able to induce a delayed apoptosis after 48 h of treatment, characterized by caspase-3 activation.