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一种新型开环烯二炔的设计、合成及细胞毒性研究

    通讯作者: 胡爱国, hagmhsn@ecust.edu.cn
  • 基金项目: 国家自然科学基金项目(21474027)

  • 中图分类号: O621.3

Design, Synthesis and Cytotoxicity Study of a Novel Acyclic Enediyne

    Corresponding author: HU Ai-guo, hagmhsn@ecust.edu.cn
  • CLC number: O621.3

  • 摘要: 通过Sonogashira反应合成了一种以马来酰亚胺为主体结构,炔基带有两个对称烷基链的烯二炔化合物。该烯二炔在适度加热的情况下能够发生Bergman环化反应,产生芳基双自由基。通过红外光谱分析确认反应后碳碳叁键信号峰消失;利用自由基捕捉技术获得了单N-叔丁基-α-苯基硝酮(PBN)加成产物和双PBN加成产物,并通过电子顺磁共振波谱检测到了这两种PBN加合物的自由基信号,说明烯二炔发生了Bergman环化反应。MTT法细胞活性实验证实该小分子烯二炔对肿瘤细胞的半抑制浓度在18 μmol/L左右,显示出烯二炔对肿瘤细胞具有良好的抗增殖能力。这为以后设计合成高活性的开环型烯二炔抗生素提供了新的思路。
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出版历程
  • 收稿日期:  2016-04-19
  • 刊出日期:  2017-03-02

一种新型开环烯二炔的设计、合成及细胞毒性研究

    通讯作者: 胡爱国, hagmhsn@ecust.edu.cn
  • 1. 华东理工大学材料科学与工程学院, 上海市先进聚合物材料重点实验室, 上海 200237
基金项目:  国家自然科学基金项目(21474027)

摘要: 通过Sonogashira反应合成了一种以马来酰亚胺为主体结构,炔基带有两个对称烷基链的烯二炔化合物。该烯二炔在适度加热的情况下能够发生Bergman环化反应,产生芳基双自由基。通过红外光谱分析确认反应后碳碳叁键信号峰消失;利用自由基捕捉技术获得了单N-叔丁基-α-苯基硝酮(PBN)加成产物和双PBN加成产物,并通过电子顺磁共振波谱检测到了这两种PBN加合物的自由基信号,说明烯二炔发生了Bergman环化反应。MTT法细胞活性实验证实该小分子烯二炔对肿瘤细胞的半抑制浓度在18 μmol/L左右,显示出烯二炔对肿瘤细胞具有良好的抗增殖能力。这为以后设计合成高活性的开环型烯二炔抗生素提供了新的思路。

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