新型喹啉衍生物的合成及其性质研究

【作者】 陈杏芬；

【导师】 杨定乔；

【作者基本信息】 华南师范大学 ， 有机化学， 2007， 硕士

【摘要】 本文首先综述了喹啉衍生物的应用研究进展。根据文献的查阅，我们设计合成四种新的双喹啉衍生物—6，7-二氢-二苯[b，j][1，10]喹啉衍生物，采用的是Friedl（?）nder合成法。我们分别以藜芦醛（1a）、2，5-二甲氧基苯甲醛（1b）、胡椒醛（1c）为起始原料，经硝酸和乙酸酐硝化得到不同取代的邻硝基苯甲醛（2a-2c），再用铁粉和稀盐酸还原（2a-2c）和邻硝基苯甲醛（2d）中的硝基，从而制得不同取代的邻氨基苯甲醛中间体（3a-3d）。四种中间体（3a-3d）分别与1，2-环己二酮（4）进行Friedl（?）nder缩合反应，合成了四种取代基不同的6，7-二氢-二苯[b，j][1，10]喹啉衍生物（5a-5d）。所合成的新喹啉衍生物均通过MS，UV，IR，¹H NMR和¹³C NMR的结构测定和表征，确证了所合成的化合物与目标化合物的结构相符。其中化合物（5a）和（5c）测定了荧光光谱性质；化合物（5a）和（5d）培养了单晶，并用X-ray进行晶体结构测定。本文采用紫外滴定光谱法和荧光滴定光谱法研究了双喹啉类化合物（5a-5d）与小牛胸腺（CT）DNA的相互作用。结果显示：四种目标化合物均能在一定的浓度范围内与CT DNA发生相互作用。本文还对合成反应中的反应条件的多个方面进行了讨论，如溶剂，催化剂，反应温度，反应时间及目标化合物的溶解性等。并对目标化合物的结构波谱数据进行了较详细的解析和讨论。更多还原

【Abstract】 In this paper, the progress of quinoline derivatives in application is summarized. According to a lot of materials, we designed the synthetic route for four novel bisquinolines-6,7-dihydro- dibenzo[b,j][1,10]quinoline derivatives and they have been synthesized successfully by Friedlander condensation reaction.At the room temperature, 2-nitro-4,5-dimethoxy-benzaldehyde (2a), 2-nitro-3,6-dimethoxy-benzaldehyde (2b) and 6-nitropiperonal (2c) have been prepared from veratraldehyde (la), 2,5-dimethoxy-benzaldehyde(1b) and piperonal (1c) in the presence of acetic anhydride with nitric acid. The reduction of (2a-2c) and o-nitrobenzadehyde (2d) with iron powder afforded the corresponding amino aldehyde (3a-3d). With sodium ethoxide as catalyst, the compounds (3a-3d) condensed with 1,2-cyclohexanedione (4) respectively to generate four novel quinoline derivatives (5a-5d). The target compounds (5a-5d) were identified and characterized by MS,UV, IR, 1H NMR and 13C NMR. The optical behavior of (5a) and (5c) were investigated by Fluorescence spectra. The single crystal data of (5a) and (5d) were obtained by X-ray technique and their structures were determined further.In this paper, the binding activities toward calf thymus (CT) DNA of (5a-5d) were investigated by means of spectrophotometric and spectrofluorimetric titrations. The results indicated that all the four target compounds exhibited DNA-binding affinities in the definited concentration.The reaction conditions of Friedlander condensation reaction such as solvent, catalyst, reaction temperature, time and so on were discussed, and every kind of spectrums of target compounds were explained in detail.更多还原