联噻唑腙类化合物的合成及性质研究

发布时间：2018-06-27 13:43

本文选题：联噻唑 + 腙　；参考：《郑州大学》2017年硕士论文

【摘要】：联噻唑具有较大的π共轭体系、良好的金属配位能力和电子传输水平,可应用于光电材料、DNA断裂切割、有机磁性材料等方面。腙含R-C=N-N-R结构单元,其结构特殊可组合性强,在分析检测、农业、医药、功能材料等领域应用广泛。基于联噻唑和腙所具有的性质,联噻唑-腙类化合物的设计合成对于荧光材料的研究、生物活性药物的设计都有着重要意义。本文合成了3个系列共15个新的联噻唑腙类化合物BhL_1~BhL_(15),研究了它们的光学性质和生物活性。1.以丁二酮、液溴、氨基硫脲以及不同种类的苯甲醛为原料,通过Hantzsch缩合反应合成了15个新的联噻唑腙类化合物。采用核磁共振氢谱、碳谱、质谱、元素分析、红外等方法对它们进行了表征,并得到了两个目标化合物BhL_1、BhL6的单晶结构。2.紫外性质表明,化合物BhL_1~BhL_(15)在258-359 nm处的紫外吸收峰归属于分子内的π-π*轨道跃迁。荧光性质表明,该类化合物具有较好的荧光性能。含卤素取代的化合物紫外和荧光光谱出现红移现象。量化计算从理论上解释了化合物的光学性质。3.金属离子识别测试表明,加入Fe~(3+)后化合物BhL_1~BhL_(15)均发生荧光猝灭。化合物BhL_(15)对Cu~(2+)有裸眼识别作用,加入Cu~(2+)溶液由无色变为黄色,BhL_(15)对Cu~(2+)的识别具有专一性且不受其它金属阳离子干扰,Job法测得络合比为1:1,检测限达3.74mM。4.抗菌活性表明,间位含-Cl、-OH取代的化合物,即BhL8和BhL_10对革兰氏阳性菌有一定程度的抑制作用。抗肿瘤活性表明,化合物对不同的肿瘤细胞抑制作用不同。其中BhL5对人食管癌细胞EC-9706的抑制作用最明显IC50值为11.76mM。间位系列的化合物抗肿瘤活性优于对位和邻位,其中间位含-Cl取代的化合物表现出最好的抗肿瘤活性。
[Abstract]:Because of its large 蟺 conjugation system, good metal coordination ability and electron transport level, it can be used in photoelectrical materials such as DNA cleavage, organic magnetic materials and so on. Hydrazone contains R-CnN-N-R structural unit, which has a special structure and strong combinability. It is widely used in analytical detection, agriculture, medicine, functional materials and so on. Based on the properties of dithiazole and Hydrazone, the design and synthesis of dithiazole-Hydrazone compounds are of great significance for the study of fluorescent materials and the design of bioactive drugs. In this paper, three series of 15 new dithiazolizone compounds BhL _ (1) BhL _ (15) have been synthesized and their optical properties and biological activities have been studied. Fifteen new dithiazolone Hydrazone compounds were synthesized by Hantzsch condensation from succinedione, bromine, thiosemicarbazone and benzaldehyde. They were characterized by nuclear magnetic resonance (NMR), carbon spectrum, mass spectrometry, elemental analysis and IR, and the single crystal structure of two target compounds, BhL-1, BhL6, was obtained. The UV properties indicate that the UV absorption peak of the compound BhL1 / BhL15 at 258-359 nm is attributed to the intramolecular 蟺-蟺 * orbital transition. The fluorescence properties show that this kind of compounds have better fluorescence properties. The UV and fluorescence spectra of halogen-substituted compounds show red shift phenomenon. The quantitative calculation explains the optical properties of the compound theoretically. Metal ion recognition test showed that the fluorescence quenching of the compound BhL _ (15) was observed after the addition of Fe ~ (3). The compound BhL15 can recognize Cu2 by naked eyes. Adding Cu2 solution from colorless to yellow BhL15 has the specificity of recognition of Cu2, and the complexation ratio determined by Job method is 1: 1, and the detection limit is 3.74mM.4. The antimicrobial activity indicated that m-Cl-OH substituted compounds, namely, BhL8 and BhLStu10, could inhibit Gram-positive bacteria to some extent. The anti-tumor activity showed that the inhibitory effects of the compounds on different tumor cells were different. The inhibitory effect of BhL5 on human esophageal cancer cell EC-9706 was the most obvious IC50 was 11.76mM. The antineoplastic activity of the mesopotopic compounds was superior to that of the opposite and adjacent sites, and the compounds with -Cl substituents in the intermediate sites showed the best antitumor activity.
【学位授予单位】：郑州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626

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