5-((1-ethylpyrrolidin-2-yl)methyl)-4H-benzo[de]benzo[4,5]thieno[2,3-g]isoquinoline-4,6(5H)-dione | 1097136-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-((1-ethylpyrrolidin-2-yl)methyl)-4H-benzo[de]benzo[4,5]thieno[2,3-g]isoquinoline-4,6(5H)-dione
• CAS: 1097136-28-1
• 化学式: C₂₅H₂₂N₂O₂S
• 分子量: 414.528
• InChiKey: OTJYMHPRJADJEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-乙基-2-氨甲基吡咯烷 、 benzothiophenonaphthalic anhydride 以 乙醇 为溶剂， 反应 3.0h， 以83%的产率得到5-((1-ethylpyrrolidin-2-yl)methyl)-4H-benzo[de]benzo[4,5]thieno[2,3-g]isoquinoline-4,6(5H)-dione
  参考文献：
  名称：

  Naphthalimide intercalators with chiral amino side chains: Effects of chirality on DNA binding, photodamage and antitumor cytotoxicity

  摘要：

  Several novel heterocyclic-fused naphthalimides intercalators with chiral amino side chains were investigated. Their side chains' chiral configuration determines DNA binding activities in the order: S-enantiomers > R-enantiomers. And their DNA photodamaging activities were in good agreement with their DNA binding constants, the S-enantiomers could photocleave circular supercoiled pBR322 DNA more ef.ciently than their R-enantiomers. S-enantiomer B-3 could photodamage DNA at 0.2 mu M and cleave supercoiled plasmid DNA from form I to form II completely at 50 mu M. Almost all of these intercalators showed effective cytoxicities against human lung cancer cells and murine leukemia cells. S-enantiomers showed different antitumor cytotoxicity by comparison with R-enantiomers. This work may provide additional information for the role of amino side chains on intercalators as antitumor agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.104