2-[3-(1,3-Dioxoisoindol-2-yl)propyl]benzo[de]isoquinoline-1,3-dione | 1223044-82-3

• 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: 2-[3-(1,3-Dioxoisoindol-2-yl)propyl]benzo[de]isoquinoline-1,3-dione
• CAS: 1223044-82-3
• 化学式: C₂₃H₁₆N₂O₄
• 分子量: 384.391
• InChiKey: IJZPWCHTIIRWCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[3-(1,3-Dioxoisoindol-2-yl)propyl]benzo[de]isoquinoline-1,3-dione 在 一水合肼 、 盐酸 作用下， 以 乙醇 、 乙醚 、 水 为溶剂， 反应 12.0h， 以26%的产率得到2-(3-Aminopropyl)benzo[de]isoquinoline-1,3-dione;hydrochloride
  参考文献：
  名称：

  Synthesis, cytotoxicity and DNA-binding of novel bisnaphthalimidopropyl derivatives in breast cancer MDA-MB-231 cells

  摘要：

  New naphthalimidopropyl, bisphthalimidopropyl and bisnaphthalimidopropyl (BNIP) derivatives were synthesised and characterised. Their interactions with Calf Thymus DNA were studied by UV spectrophotometric analysis and a competitive Ethidium bromide displacement assay. Cytotoxicity was determined by MTT assay in a breast cell system (MDA-MB-231 and MCF-10A cells). All BNIPs exhibited strong DNA-binding properties and cytotoxic activity with IC(50) values in the range of 0.83-12.68 mu M (24 and 48 h treatment). In addition, the uptake of BNIP derivatives within cancer cells was not via utilisation of the MGBG polyamine transporter. Put together the results confirm that the presence of the bisnaphthalimidopropyl and alkyl linker functionality are crucial for exerting DNA-binding and cytotoxic properties, hence demonstrating promise in their further development as potential anti cancer agents. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.047
• 作为产物：
  描述：

  potassium phtalimide 、 N-<3-(4-methylbenzenesulfonoxy)propyl>naphthalimide 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以65%的产率得到2-[3-(1,3-Dioxoisoindol-2-yl)propyl]benzo[de]isoquinoline-1,3-dione
  参考文献：
  名称：

  Synthesis, cytotoxicity and DNA-binding of novel bisnaphthalimidopropyl derivatives in breast cancer MDA-MB-231 cells

  摘要：

  New naphthalimidopropyl, bisphthalimidopropyl and bisnaphthalimidopropyl (BNIP) derivatives were synthesised and characterised. Their interactions with Calf Thymus DNA were studied by UV spectrophotometric analysis and a competitive Ethidium bromide displacement assay. Cytotoxicity was determined by MTT assay in a breast cell system (MDA-MB-231 and MCF-10A cells). All BNIPs exhibited strong DNA-binding properties and cytotoxic activity with IC(50) values in the range of 0.83-12.68 mu M (24 and 48 h treatment). In addition, the uptake of BNIP derivatives within cancer cells was not via utilisation of the MGBG polyamine transporter. Put together the results confirm that the presence of the bisnaphthalimidopropyl and alkyl linker functionality are crucial for exerting DNA-binding and cytotoxic properties, hence demonstrating promise in their further development as potential anti cancer agents. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.047

文献信息

• Synthesis, cytotoxicity and DNA-binding of novel bisnaphthalimidopropyl derivatives in breast cancer MDA-MB-231 cells
  作者：Gemma A. Barron、Giovanna Bermano、Amanda Gordon、Paul Kong Thoo Lin

  DOI：10.1016/j.ejmech.2009.12.047

  日期：2010.4

  New naphthalimidopropyl, bisphthalimidopropyl and bisnaphthalimidopropyl (BNIP) derivatives were synthesised and characterised. Their interactions with Calf Thymus DNA were studied by UV spectrophotometric analysis and a competitive Ethidium bromide displacement assay. Cytotoxicity was determined by MTT assay in a breast cell system (MDA-MB-231 and MCF-10A cells). All BNIPs exhibited strong DNA-binding properties and cytotoxic activity with IC(50) values in the range of 0.83-12.68 mu M (24 and 48 h treatment). In addition, the uptake of BNIP derivatives within cancer cells was not via utilisation of the MGBG polyamine transporter. Put together the results confirm that the presence of the bisnaphthalimidopropyl and alkyl linker functionality are crucial for exerting DNA-binding and cytotoxic properties, hence demonstrating promise in their further development as potential anti cancer agents. (C) 2009 Elsevier Masson SAS. All rights reserved.