新型吡嗪酮类席夫碱化合物的设计合成及抑菌性能研究

【作者】 李娜；

【导师】 赵建社；

【作者基本信息】 西北大学 ， 无机化学， 2009， 硕士

【摘要】 Schiff碱是一类非常重要含氮配体,它的-RC=N-双键官能团使其具有易配位、易成环等特点。迄今国内外化学工作者不断开展此领域的工作,合成了各类Schiff碱及其金属配合物,研究和开发了多方面的用途。其中氮杂环Schiff碱配体及其过渡金属配合物的良好生物活性日益引起了人们的注意,因此设计合成这种Schiff碱配体及其过渡金属配合物具有重要的化学与生物学意义。本论文首次由2-乙酰基吡嗪为原料设计合成了4种吡嗪酮类Schiff碱配体。实验发现,苯胺对位取代基结构不同与2-乙酰吡嗪发生Schiff碱缩合反应活性也不相同,得到反应活性顺序为:4-甲氧基苯胺＞4-甲基苯胺＞4-氯苯胺＞4-溴苯胺。对4种Schiff碱配体进行了元素分析、核磁共振、红外、紫外光谱等方法表征。实验中对两种制备Schiff碱配体的方法(传统方法和微波方法)进行了对比。4种Schiff碱配体分别与过渡金属Fe()、Co(Ⅱ)、Ni(Ⅱ)、Cu(Ⅱ)合成了16种Schiff碱配合物,并对16种Schiff碱配合物进行了元素分析、红外、紫外光谱等表征。本论文着重研究了所得Schiff碱配体和配合物的生物活性。通过对金黄色葡萄球菌、枯草杆菌、大肠杆菌的抑菌活性测试,深入探讨了配体结构、中心金属电子效应与生物活性之间的关系。本论文还使用微波技术合成新型Schiff碱配体前躯体3-二甲氨基-1-(2-吡嗪基)-2-丙烯-1-酮。比较了反应过程中常规加热和微波加热对反应的不同影响,发现微波辐射加热条件下的反应时间大为缩短、产率有所提高。应用单因素法,通过系列实验对微波合成方法进行了深入研究,采用响应面优化法对实验条件进行科学可靠性分析,得到最佳实验条件。更多还原

【Abstract】 Schiff base is a kind of very important N-included ligand,and its functional group of -RC=N-bond is inclined to coordinated with metals and to be tinged formation.Up to the date,all kinds of Sehiff bases and their metal complexes have been synthesized and characterised by researchers,and their application have been exploited in many fields,among which nitrogenous heteroeycle Schiff bases and their metal complexes have been paid more attention due to their special use for bio-activity.Therefore,design and synthesise some new Schiff base ligands and their complexes of transition metals have much signification in chemistry and biology field.In this dissertation 2-acetylpyrazine keto Schiff base ligands have been obtained for the first time,and were characterized by elemental analysis,IR,~1HNMR and UV spectra,16 numsers of transition metal(M=Fe(Ⅲ),Co(Ⅱ),Ni(Ⅱ),Cu(Ⅱ)) complexes based on the 2-acetylpyrazine keto Schiff bases have been prepared.The effect factors of the reaction process on aniline-like structure were analyzed in terms of the experiment results,and the result obtain indicates the order of activity as follow:4-methoxyanline＞4-methyanline＞4-ehloroaniline＞4-brom-anilines.The reaction heated by traditional and microwave method was compared in this paper.The emphasis studies are focused on the biology-active of the Sehiff base ligands and their complexes.In the same time,the correlation among electronic property of central metal,the ligand structure and bio-activity are also investigated.In this paper,the precursor compounds of anticancer drug 3-dimethylamino-1-(2-pyrazineyl)-2-propylene-1-one has been synthesized by microwave-assisted process.There reaction process by traditional and microwave method was compared to each other respective.Compared with the traditional synthetic method,the same products were obtained with shorter under the microwave radiation with reaction time and in higher yield.The single-factor method and response surface methodology was employed to study the reaction effects,we performed a series of experiments under various reaction time, solvent and power,from which the optimal reaction conditions have been obtained.更多还原