双功能团1,3,4-噁二唑类荧光探针的研究.pdf

摘要

研究表明，一些含有氮、硫原子的杂环化合物在农药和医药等领域有广泛的应用价
值，例如 1,3,4-噁二唑类化合物就具有杀虫、抗菌、抗炎和抗癌等多种生物活性，同时
在电致发光器件中因具有优良的电子传输功能备受关注；另一种杂环化合物香豆素类，
具有抗癌、降压、抗心律失常和抗菌等多种生物活性。与此同时，1,3,4-噁二唑和香豆
素类化合物显著荧光性能引起人们的关注，在荧光分析和检测方面的研究十分活跃。
本文以 1,3,4-噁二唑为母体结构，基于活性亚结构拼接和生物等排的原理，引入香
豆素和芳烃两类活性单元结构，以水杨醛和丙二酸二乙酯为原料，通过酯化、氯酰化、
肼解和合环等反应步骤，设计合成了同时含有 1,3,4-噁二唑和香豆素双发光团结构的新
型荧光化合物，通过对合成出的目标化合物的光谱性质进行分析，研究引入不同种类的
取代基后对化合物荧光性能产生的影响。
以 2-(2’-氯苯基)-5-(2’-羟基苯基)-1,3,4-噁二唑为代表，通过荧光猝灭法就 1,3,4-噁二
唑类化合物对小牛胸腺 DNA 影响效应进行了初步探讨，考察了温度、时间、离子强度
对该体系荧光强度的影响，实验结果表明 1,3,4-噁二唑与 DNA 的相互作用可能为静态猝
灭过程。
以 1,3,4-噁二唑为母核，利用生物活性的叠加原理，设计合成了2 个噁二唑硫醚衍
生物，并采用抑菌区域法对化合物进行体外抗菌的活性测试。结果表明对大肠杆菌的抑
菌率都达到了 95%以上，对金黄葡萄球菌和枯草杆菌的抑菌率也达到或接近 80%以上，
都有较好的抗菌活性。

关键词：香豆素 1,3,4-噁二唑 DNA 荧光猝灭 抗菌活性
Abstract

It is well-known that some heterocyclic compounds which contain O,N and S elements，
are valuable in many fields. For example, 1,3,4-oxadiazole derivatives are reported to be with
biological activities such as pesticides, antifungal, antibacterial, and cancer treatment
materials. Besides, 1,3,4-oxadiazoles are integrated with the hole transport and used as classes
of electroluminescent materials. Meanwhile, coumarin derivatives are reported to possess the
activity of anti-cancer, blood pressure, anti-arrhythmia, antibacterial and other biological
activities, as well as with the unique photo physical property as a good fluorescent group.
Based on the connecting principle of active biological groups and the bioisosterism,
some new compounds which contain double functional units of 1,3,4-oxadiazole and
coumarin group in each molecule are designed and synthesized. The reaction was connected
with many steps such as esterification, hydrazinolysis, and cyclization reaction. The desired
structures were characterized by 1H-NMR, IR ways and thei