近年来，杂环类酰腙化合物及其金属配合物因其生理及药理活性而受到科学工作者的关注，并且已广泛应用于化学、化工、生物和医学等方面。本文将生物活性强的咪唑环和萘环引入到酰腙化合物中，合成了一系列新型杂环类酰腙化合物及其过渡金属配合物。 主要工作如下： (1) 以4-羟基苯乙酸甲酯、80%水合肼以及2-羟基-1-萘甲醛为原料合成了2-羟基-1-萘甲醛-4-羟基苯乙酰腙(C19H16N2O3•H2O，化合物I)；以咪唑-4-甲酸乙酯、80%水合肼、2-羟基-3-甲氧基苯甲醛、3-羟基-4-甲氧基苯甲醛及2-羟基-1-萘甲醛为原料，合成了2-羟基-3-甲氧基苯甲醛-咪唑-4-甲酰腙(C12H12N4O3，化合物II)，3-羟基-4-甲氧基苯甲醛-咪唑-4-甲酰腙(C12H12N4O3•H2O，化合物III)和2-羟基-1-萘甲醛-咪唑-4-甲酰腙(C15H12N4O2•CH3OH，化合物IV)，并分别在无水乙醇和甲醇溶剂中培养得到了4种化合物的单晶。X-射线单晶衍射结果说明4种酰腙化合物的晶体均属单斜晶系。 (2) 合成了2-羟基-1-萘甲醛-4-羟基苯乙酰腙C19H16N2O3•H2O 的Cu、Co、Ni和Zn硝酸盐的配合物，并通过元素分析、络合滴定和红外光谱等手段进行表征。其中Cu配合物在无水乙醇溶剂中培养出了单晶，X-射线单晶衍射结果说明晶体属于三斜晶系，P1空间群，a=7.6436(3) Å，b=8.6188(5) Å，c=13.7731(5) Å，α=72.437(4)°，β=84.718(3)°，γ=88.369(4)°，V= 861.38(7) Å3，Z=1，F(000)=454，Dc＝1.715 mg•m-3。另外3种配合物的组成推测与Cu配合物相同，化学式为[M2(C19H15N2O3)2(NO3)2]。 (3) 通过TG-DTG测试探究了4种酰腙化合物和4种化合物I与过渡金属配合物的热分解过程及热稳定性，利用Kissinger和Ozawa公式计算了它们在5.00 ℃•min-1，10.00 ℃•min-1和15.00 ℃•min-1三个不同升温速率下主要热分解阶段的热动力学参数。结果表明，4种化合物主要分解过程的最高分解峰温度范围在305~346 ℃之间，其中化合物I的分解温度最大。它们的表观活化能Ea的顺序是IV＞II＞I＞III，它们的热稳定性顺序与上述活化能大小排序一致。化合物I与过渡金属形成的配合物主要有两个热分解阶段，第一阶段的最高分解峰温度范围在280~356 ℃之间，第二阶段的最高分解峰温度范围是295~434 ℃，其中化合物I与过渡金属Zn配合物的分解温度最高。化合物I与过渡金属形成的配合物表观活化能Ea第一阶段从大到小顺序是：Cu配合物＞Ni配合物＞Zn配合物＞Co配合物；第二阶段：Ni配合物＞Co配合物＞Zn配合物＞Cu配合物。两种计算方法所得到的化合物与过渡金属配合物的活化能Ea和线性相关系数r均较为接近，配合物的热稳定性较相应酰腙化合物更高。 (4) 利用紫外可见光谱初步分析了4种酰腙化合物与CT-DNA的相互作用，化合物I~IV的结合常数Kb分别为：3.09×106 L•mol-1，4.44×105 L•mol-1，4.24×106 L•mol-1和8.54×106 L•mol-1，结果表明4种酰腙化合物与CT-DNA有较强的相互作用。 (5) 利用微量热法探讨了4种酰腙化合物、4种化合物I与过渡金属配合物和CT-DNA的相互作用。结果表明，酰腙化合物及过渡金属配合物与CT-DNA的相互作用均为吸热反应，化合物I~IV的反应焓变值分别为12.2 kJ•mol-1，3.57 kJ•mol-1，3.39 kJ•mol-1和4.49 kJ•mol-1。化合物I与过渡金属Cu、Co、Ni和Zn配合物的反应焓变值分别为30.3 kJ•mol-1，10.3 kJ•mol-1，30.8 kJ•mol-1和20.3 kJ•mol-1。从数据结果可以看出，化合物I的反应焓变值最大，它与过渡金属形成的配合物和CT-DNA的结合能力优于相应配体，其中Ni配合物的反应焓变值最大。

In recent years, acylhydrazones compounds containing heterocyclic ring and their metal complexes have been concerned by scientists because of their unique physiological and pharmacological activity, and widely used in many aspects such as chemistry, chemical engineering, biology and medicine. In this paper, we introduced imidazole ring and naphthalene ring which have strong biological activity into acylhydrazone compounds to synthsis a series of novel acylhydrazone compounds and transition metal complexes. The main researches are as follows: (1) The 2-hydroxy-1-naphthaldehyde-(4’-hydroxy) phenylacetyl hydrazone (C19H16N2O3•H2O, compound I) was prepared from 2-hydroxy-1-naphthaldehyde, hydrazine monohydrate (80%) and methyl 4-hydroxyphenylacetate. The 1H-imidazole-4-carboxylic acid (2-hydroxy-3-methoxy-benzylidene)-hydrazone (C12H12N4O3, compound II), 1H-imidazole-4-carboxylic acid (3-hydroxy-4-methoxy-benzylidene)-hydrazone (C12H12N4O3•H2O, compound III) and 1H-imidazole-4-carboxylic acid (2-hydroxy-naphthalen-1-ylmethylene)-hydrazone (C15H12N4O2•CH3OH, compound IV) were prepared from the ethyl 1H-imidazole-4-carboxylate, hydrazine monohydrate (80%), 2-hydroxy-3-methoxy benzaldehyde, 3-hydroxy-4-methoxybenzaldehyde and 2-hydroxy-1-naphthaldehyde. Their single crystals were obtained by slow evaporation of ethanol or methanol solution, respectively. The results of X-ray crystal diffraction show that four compounds all crystallize in the monoclinic space group. (2) The transition metal complexes of C19H16N2O3•H2O were synthesized and characterized by elemental analysis, complexometric titration and FT-IR spectra. The single crystal of Cu complex was obtained by slow evaporation from its ethanol solution, and the restlts of X-ray crystal diffraction showed that the complex crystallizes in the triclinic space group. It was found that the possible structures of the other three complexes were the same with Cu complex, chemical formula is [M2(C19H15N2O3)2(NO3)2]. (3) The thermal decomposition processes of four acylhydrazones and four transition metal complexes with compound I at the heating rates of 5.00 ℃•min-1, 10.00 ℃•min-1 and 15.00 ℃•min-1 were measured by TG-DTG. The results showed that the mainly maximum decomposition peak temperature of four compounds ranged from 305 to 346 ℃, which the decomposition temperature of compound I is the highest. Their apparent activation energies were calculated by Kissinger’s and Ozawa’s equations. The sequence of their apparent activation energies is IV＞II＞I＞III, indicating that the sequence of their thermal abilities agree with the former. The complexes have two main decomposition stages. The maximum decomposition peak temperature of the first stage ranged from 280 to 356 ℃, and the second stage ranged from 295 to 434 ℃, among which the decomposition temperature of Zn complex is the highest. The sequence of the apparent activation energies of the first stage is Cu complex＞Ni complex＞Zn complex＞Co complex, and the sequence of the second stage is Ni complex＞Co complex＞Zn complex＞Cu complex. In general, the thermal stability of the complexes is higher than the corresponding ligand. (4) The abilities of four acylhydrazones binding to CT-DNA were investigated by UV-Vis spectra. The binding constants of compounds I~IV were 3.09×106 L•mol-1, 4.44×105 L•mol-1, 4.24×106 L•mol-1 and 8.54×106 L•mol-1, respectively. It was found that the binding abilities of four acylhydrazones with CT-DNA were strong. (5) The interaction processes of four acylhydrazones and four transition metal complexes with CT-DNA were investigated by microcalorimeter. The enthalpy changes of compounds I~IV are 12.2 kJ•mol-1, 3.57 kJ•mol-1, 3.39 kJ•mol-1 and 4.49 kJ•mol-1. The enthalpy changes of Cu, Co, Ni and Zn complexes are 30.3 kJ•mol-1, 10.3 kJ•mol-1, 30.8 kJ•mol-1 and 20.3 kJ•mol-1. It was shown that the binding ability of the four complexes with CT-DNA were better than the corresponding ligand.