4-thiophenyl-N-(N',N'-dimethylaminoethyl)-1,8-naphthalimide | 1374842-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-thiophenyl-N-(N',N'-dimethylaminoethyl)-1,8-naphthalimide
• CAS: 1374842-21-3
• 化学式: C₂₂H₂₀N₂O₂S
• 分子量: 376.479
• InChiKey: OMRNRSDUYOHYKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  4-phenylthio-1,8-naphthalic anhydride 、 N,N-二甲基乙二胺 以 乙醇 为溶剂， 反应 7.0h， 以63%的产率得到4-thiophenyl-N-(N',N'-dimethylaminoethyl)-1,8-naphthalimide
  参考文献：
  名称：

  Fluorescence properties and antiproliferative effects of mono-, bis-, and tris- thiophenylnaphthalimides: Results of a comparative pilot study

  摘要：

  A series of mono-, bis- and trisnaphthalimides with different substituents on the naphthalimide ring system was prepared. For compounds containing a thiophenyl substituent fluorescence spectroscopic measurements were performed and unexpectedly showed an increase in fluorescence emission for the bis- and trisnaphthalimide derivatives in phosphate buffered saline. Additional fluorescence microscopic experiments indicated an efficient cellular uptake of the thiophenyl substituted compound 1c into cultured tumor cells. Experiments on the inhibition of tumor cell proliferation were performed in MCF-7 breast adenocarcinoma and HT-29 colon carcinoma cells and confirmed derivatives containing a nitro substituent as the most active compounds. Compound 1c demonstrated potential as photoinducable antitumor agent. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotobiol.2011.06.012