1-(3'-(1'',8"-naphthalimid-N"-yl))-propyl-3-ethylimidazolium iodide | 1228963-71-0

• 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: 1-(3'-(1'',8"-naphthalimid-N"-yl))-propyl-3-ethylimidazolium iodide
• 英文别名: 2-[3-(3-Ethylimidazol-1-ium-1-yl)propyl]benzo[de]isoquinoline-1,3-dione;iodide；2-[3-(3-ethylimidazol-1-ium-1-yl)propyl]benzo[de]isoquinoline-1,3-dione;iodide
• CAS: 1228963-71-0
• 化学式: C₂₀H₂₀N₃O₂*I
• 分子量: 461.302
• InChiKey: NORGXTDZIWOONB-UHFFFAOYSA-M

反应信息

• 作为反应物：
  描述：

  1-(3'-(1'',8"-naphthalimid-N"-yl))-propyl-3-ethylimidazolium iodide 在 ammonium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以70%的产率得到
  参考文献：
  名称：

  The synthesis of 1,8-naphthalimide groups containing imidazolium salts/ionic liquids using I−, PF6−, TFSI− anions and their photophysical, electrochemical and thermal properties

  摘要：

  1,8-Naphthalimide groups containing imidazolium iodide salts of different alkyl chain length on the imidazole group were synthesized. Hexafluorophosphate and bis(trifluoromethanesulfonyl)imide salts were obtained by ion exchange reactions. The synthesized salts were characterized using a variety of spectroscopic techniques. Fluorescence emission quenching of iodide and bis(trifluoromethanesulfonyl) imide salts were studied using a ruthenium dye, whilst that of hexafluorophosphate salts were performed using tris(8-hydroxyquinoline)aluminum. Calculated fluorescence quenching rate constants were as high as 10(14)M(-1)s(-1) and values of the Gibbs free energy of electron transfer were [-32.04/-33.681],[-17.52/-20.741] and [-26.50/-30.89] kcal mol(-1) for the iodide, hexafluorophosphate and bis(trifluoromethanesulfonyl) imide salts, respectively. The thermal stability of the synthesized salts was high especially in the case of bis (trifluoromethanesulfonyl)imide salts for which values of 470-498 degrees C were achieved. Photostability studies of hexafluorophosphate and bis(trifluoromethanesulfonyl)imide salts were also performed: calculated photodegradation half-life values ranged from 19.25 to 48.12 h. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.01.005
• 作为产物：
  描述：

  1,8-萘二甲酸酐 以 乙酸乙酯 、 甲苯 为溶剂， 反应 8.0h， 生成 1-(3'-(1'',8"-naphthalimid-N"-yl))-propyl-3-ethylimidazolium iodide
  参考文献：
  名称：

  金（I）N-杂环卡宾配合物与萘二甲酰亚胺配体作为硫氧还蛋白还原酶抑制剂和DNA嵌入剂的组合

  摘要：

  制备了由金（I）N-杂环卡宾（NHC）部分和萘二甲酰亚胺组成的有机金属共轭物，并作为与DNA和二硫键还原酶硫氧还蛋白还原酶（TrxR）相互作用的细胞毒剂进行了研究。该复合物是与其萘二甲酰亚胺部分结构相关的有效DNA嵌入剂，由于掺入了gold（I）部分而抑制了TrxR，并在MCF-7乳腺癌和HT-29结肠腺癌细胞中触发了有效的细胞毒性作用。注意到最具细胞毒性的复合物，氯离子[1-（3'-（4'-乙硫基-1''，8''-萘二甲酰亚胺-N ''-基））-丙基-3对肿瘤细胞代谢有强烈影响。-甲基-咪唑-2-亚烷基]金（I）（4 d）。总之，萘二甲酰亚胺与金（I）NHC部分的结合为设计具有多种作用方式的生物有机金属抗癌剂提供了有用的策略。

  DOI：

  10.1002/cmdc.201402049

文献信息

• Metal NHC Complexes with Naphthalimide Ligands as DNA-Interacting Antiproliferative Agents
  作者：Wojciech Streciwilk、Alessio Terenzi、Rainer Misgeld、Corazon Frias、Peter G. Jones、Aram Prokop、Bernhard K. Keppler、Ingo Ott

  DOI：10.1002/cmdc.201600557

  日期：2017.2.3

  Naphthalimide‐based N‐heterocyclic carbene (NHC) complexes of the type [(1,5‐cyclooctadiene)(NHC)RhCl)] (4 a–c), [(p‐cymene)(NHC)RuCl2)] (5 a–c), and [(NHC)CuBr] (6 a–c) were synthesized and investigated as antiproliferative agents that target DNA. The cytotoxic effects were largely driven by the naphthalimide structure, which is a DNA‐intercalating moiety. Regarding the metal center, the highest activities

  [（1,5-环辛二烯）（NHC）RhCl）]（4 a – c），[（对苯甲基）（NHC）RuCl 2）型萘二甲酰亚胺基N杂环卡宾（NHC）络合物（5 a – c）和[（NHC）CuBr]（6 a – c）被合成并作为靶向DNA的抗增殖剂进行了研究。细胞毒性作用主要由萘嵌二酰亚胺结构驱动，萘嵌二苯结构是DNA插入部分。关于金属中心，铑配合物具有最高的活性，而钌衍生物的细胞毒活性则明显较低。选定配合物4 b的NHC配体的稳定配位确认了溶液中的5b和5b，并通过UV / Vis光谱，质谱和圆二色性研究了它们的DNA结合特性。高DNA结合常数表明，对于所有选定的基于萘二甲酰亚胺的复合物，DNA均能稳定地嵌入到DNA中。在铑配合物4b的情况下观察到特别有效的结合。对4b的更详细的生物学研究表明，它对多药耐药的Nalm-6细胞具有积极的作用，并证实了线粒体途径在4b诱导的细胞凋亡中具有重要作用。