含氮杂环配体及其配合物的合成、表征与生物活性研究
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摘要
本文以含氮五元杂环化合物1-苯基-3-甲基-2-吡唑啉-5-酮(简称PMP)、含氮六元杂环化合物1-(2-氨基乙基)-哌嗪(简称AEP)和1,4-二(3-氨基丙基)哌嗪(简称BAPP)为原料,合成了8个相应的衍生物,并以此为配体,使用溶液法或溶剂热法合成9个过渡金属配合物。采用元素分析、红外光谱、核磁共振氢谱和碳谱、紫外光谱、固体荧光光谱等分析手段对产物进行表征,并通过单晶X-射线衍射解析了15个化合物的晶体结构,对部分化合物的热稳定性及电化学性质进行了研究。分别利用琼脂平板扩散抑菌法、粘度法、紫外可见吸收光谱法初步研究了部分产物的抑菌活性、与生物大分子即牛血清白蛋白(BSA)及小牛胸腺DNA (CT-DNA)的相互作用。
利用乙酰乙酸乙酯和苯肼的缩合成环反应,制备了五元氮杂环配体PMP。用溶剂热法处理不同摩尔比的PMP与乙腈,得到2个不同的化合物：烯醇式PMP(1)和4.4-次甲基-双(1-苯基-3-甲基-2-吡唑啉-5-酮)(2)。用PMP与乙二胺在甲醇溶液中反应合成了1个有机盐二(5-甲基-3-氧-2-苯基-2,3-二氢吡唑)化乙二铵(3)。对所得产物进行了元素分析、红外和固体荧光光谱、核磁共振氢谱和碳谱、差热-热重分析等表征,并通过单晶X-射线衍射解析了3个化合物的晶体结构。
以PMP为配体,采用溶液法分别与氯化锌、水合醋酸锌、水合氯化镉、水合醋酸镉等金属盐反应,制备了4个PMP过渡金属配合物,并培养出其中3个配合物的单晶[Zn(PMP)2C1]_n(4)、[Cd(PMP)2]n (6)和[Cd2(PMP)2Cl_4]n (7).产物经过多种谱学手段表征确证,并利用差热-热重分析和循环伏安法研究了这些配合物的热稳定性及电化学性质。同时,研究了部分产物的生物活性,即抑菌活性、与BSA及CT-DNA的相互作用。单晶X-射线衍射分析结果表明配合物(4)是一维链状配位聚合物,配合物(6)是三维配位聚合物,配合物(7)是二维梯形配位聚合物。
在PMP存在下,采用溶液法,用二乙烯三胺(dien)分别与氯化锌、水合硝酸铜反应合成了锌配合物[Zn2(dien)2C1_4] (8)和铜配位聚合物{[Cu(dien)NO_3]NO_3}n(9)。采用元素分析、红外光谱、单晶X-射线衍射等手段对产物进行了结构表征,利用差热-热重、循环伏安法研究了它们的热稳定性、电化学性质。
在五元氮杂环5,5-二甲基海因(简称DMH)存在下,用溶剂热法处理水合氯化铜与乙腈的混合物,制备出1个具有笼状结构的双核铜配合物[Cu2C1_2(μ-Ac)4] (H_3C_2ONH)2(10)。采用元素分析、红外光谱及单晶X-射线衍射方法对其结构进行了表征,利用循环伏安法研究了其电化学行为。
利用BAPP与丙烯腈的亲核加成反应合成了一个新型的含哌嗪环四腈化合物,N,N, N',N'-四(2-氰基乙基)-1,4-二(3-氨基丙基)哌嗪(11),利用元素分析、红外光谱、核磁共振氢谱、差热-热重分析、单晶X-射线衍射等手段对产物进行了表征。
利用BAPP与多种芳香醛或丹皮酚的缩合反应制备了5个Schiff碱化合物[双对羟基苯甲醛缩BAPP Schiff碱(12)、双水杨醛缩BAPP Schiff碱(13)、双对二甲氨基苯甲醛缩BAPP Schiff碱(14)和双丹皮酚缩BAPP Schiff碱(15)]。利用AEP、丹皮酚与水合硝酸铜反应,或BAPP、水杨醛与氯化锌反应分别制得2个Schiff碱铜、锌配合物[丹皮酚缩AEPSchiff碱铜配合物(16)和二水杨醛合双水杨醛缩BAPP Schiff碱双核锌配合物(17)]。分别采用元素分析、红外光谱、核磁共振氢谱和碳谱、紫外光谱、差热-热重等手段对产物进行了表征,并通过单晶X-射线衍射解析了其中6个化合物的晶体结构。利用循环伏安法研究了铜配合物(16)的电化学性质。研究了部分含哌嗪环化合物的抑菌活性、与BSA及CT-DNA的相互作用。
In this paper, eight derivatives of five-or six-membered nitrogen-containing heterocyclic compounds of 1-phenyl-3-methyl-2-pyrazolin-5-one (namely PMP),1-(2-aminoethyl)-piperazine (namely AEP) and 1,4-bis(3-aminopropyl)piperazine (namely BAPP) were synthesized. And with these derivatives used as ligands, nine transition metal complexes were synthesized by classical solution method or solvothermal method. These compounds were characterized by elemental analysis, IR,'H NMR,13C NMR, UV-vis and fluorescent spectrum. The crystal structures of fifteen compounds were determined by single-crystal X-ray diffraction. The thermal stabilities of some compounds were studied by TG-DTA method and their electrochemical properties were also investigated by cyclic voltammetry. Furthermore, the biological activities such as antibacterial activity, interaction with Bovine Serum Albumin (BSA) and calf thymus DNA (CT-DNA) for some compounds were investigated preliminary by the agar diffusion method, electronic absorption spectroscopy and viscometry, respectively.
Five-membered azaheterocyclic ligand PMP was synthesized by the reaction of acetylacetic ester with phenylhydrazine. With PMP used as reactant, two compounds, PMP (1) in enol form and 4,4'-methenyl-bis(1-phenyl-3-methyl-2-pyrazolin-5-one) (2), were obtained respectively under solvothermal condition in the presence of different volume of acetonitrile. Another new compound, Ethylenediammonium bis(5-methyl-3-oxo-2-phenyl-2,3-dihydro-pyrazol-1-ide) (3), was prepared by the reaction of PMP with ethylenediamine in methanol solution. Their structures were confirmed by elemental analysis, IR,'H NMR,13C NMR spectrum, TG-DTA and single-crystal X-ray diffraction analysis.
Four transition metal complexes of PMP were prepared by the reaction of PMP with zinc chloride, zinc acetate hydrate, cadmium chloride hydrate and cadmium acetate hydrate in methanol solution, respectively. And three single crystals of these complexes, [Zn(PMP)2Cl]n (4)、[Cd(PMP)2]n (6) and [Cd2(PMP)2Cl4]n (7), were also obtained. These complexes were characterized by spectral analysis. Their thermal stabilities were studied by TG-DTA method and their electrochemical properties were also investigated by cyclic voltammetry. The biological activities for some PMP complexes were also preliminary studied. The single-crystal X-ray diffraction revealed that complex (4) is 1-D chain coordination polymer, complex (6) 3-D coordination polymer and complex (7) 2-D ladder coordination polymer.
Two complexes, [Zn2(dien)2Cl4] (8) and{[Cu(dien)NO3]NO3}_n(9), were obtained by the reaction of diethylenetriamine with zinc chloride or copper nitrate hydrate, respectively, in the presence of PMP in methanol solution. The structures of the two complexes were confirmed by elemental analysis, IR spectrum and single-crystal X-ray diffraction. Furthermore, their thermal stabilities were studied by TG-DTA method and their electrochemical properties were investigated by cyclic voltammetry.
The solvothermal treatment of the mixture of copper chloride dihydrate and acetonitrile in the presence of 5,5-dimethyl-imidazolidine-2,4-dione (namely DMH) resulted in the formation of a new acetate-bridged dinuclear copper complex, [Cu2Cl2(μ-Ac)4](H3C2ONH)2 (10). The complex was characterized by elemental analysis, IR spectrum and single-crystal X-ray diffraction, and its electrochemical property was also studied by cyclic voltammetry.
A novel polynitrile containing piperazine ring, N,N,N',N'-tetra(2-cyanoethyl)-1,4-bis-(3-aminopropyl)piperazine (11), was synthesized by the nucleophilic addition reaction of BAPP and acrylonitrile for the first time. Compound (11) was characterized by elemental analysis, IR,~1H NMR spectrum and TG-DTA analysis, and its crystal structure was determined by single-crystal X-ray diffraction.
Five Schiff base compounds, bis(p-hydroxylbenzaldehyde)-BAPP (12), bis(salicylal)-BAPP (13), bis(p-dimethylaminobenzaldehyde)-BAPP (14) and bis(paeonol)-BAPP (15), were synthesized by condensation of BAPP with p-hydroxylbenzaldehyde, salicylal, p-dimethylaminobenzaldehyde and paeonol, respectively. And two complexes, copper paeonol-AEP Schiff base complex (16) and dinuclear zinc bis(salicyal)-BAPP Schiff base complex (17), were obtained by the reaction of AEP, paeonol and copper nitrate dihydrate or by the reaction of salicyal, BAPP and zinc chloride, respectively. These compounds were characterized by elemental analysis, spectral analysis and TG-DTA method, and the crystal structures of six compounds were determined by single-crystal X-ray diffraction. The electrochemical behavior of complex (16) was studied by cyclic voltammetry. Moreover, antibacterial activities and interaction with BSA and CT-DNA for some compounds containing piperazine ring were also investigated.
利用乙酰乙酸乙酯和苯肼的缩合成环反应,制备了五元氮杂环配体PMP。用溶剂热法处理不同摩尔比的PMP与乙腈,得到2个不同的化合物：烯醇式PMP(1)和4.4-次甲基-双(1-苯基-3-甲基-2-吡唑啉-5-酮)(2)。用PMP与乙二胺在甲醇溶液中反应合成了1个有机盐二(5-甲基-3-氧-2-苯基-2,3-二氢吡唑)化乙二铵(3)。对所得产物进行了元素分析、红外和固体荧光光谱、核磁共振氢谱和碳谱、差热-热重分析等表征,并通过单晶X-射线衍射解析了3个化合物的晶体结构。
以PMP为配体,采用溶液法分别与氯化锌、水合醋酸锌、水合氯化镉、水合醋酸镉等金属盐反应,制备了4个PMP过渡金属配合物,并培养出其中3个配合物的单晶[Zn(PMP)2C1]_n(4)、[Cd(PMP)2]n (6)和[Cd2(PMP)2Cl_4]n (7).产物经过多种谱学手段表征确证,并利用差热-热重分析和循环伏安法研究了这些配合物的热稳定性及电化学性质。同时,研究了部分产物的生物活性,即抑菌活性、与BSA及CT-DNA的相互作用。单晶X-射线衍射分析结果表明配合物(4)是一维链状配位聚合物,配合物(6)是三维配位聚合物,配合物(7)是二维梯形配位聚合物。
在PMP存在下,采用溶液法,用二乙烯三胺(dien)分别与氯化锌、水合硝酸铜反应合成了锌配合物[Zn2(dien)2C1_4] (8)和铜配位聚合物{[Cu(dien)NO_3]NO_3}n(9)。采用元素分析、红外光谱、单晶X-射线衍射等手段对产物进行了结构表征,利用差热-热重、循环伏安法研究了它们的热稳定性、电化学性质。
在五元氮杂环5,5-二甲基海因(简称DMH)存在下,用溶剂热法处理水合氯化铜与乙腈的混合物,制备出1个具有笼状结构的双核铜配合物[Cu2C1_2(μ-Ac)4] (H_3C_2ONH)2(10)。采用元素分析、红外光谱及单晶X-射线衍射方法对其结构进行了表征,利用循环伏安法研究了其电化学行为。
利用BAPP与丙烯腈的亲核加成反应合成了一个新型的含哌嗪环四腈化合物,N,N, N',N'-四(2-氰基乙基)-1,4-二(3-氨基丙基)哌嗪(11),利用元素分析、红外光谱、核磁共振氢谱、差热-热重分析、单晶X-射线衍射等手段对产物进行了表征。
利用BAPP与多种芳香醛或丹皮酚的缩合反应制备了5个Schiff碱化合物[双对羟基苯甲醛缩BAPP Schiff碱(12)、双水杨醛缩BAPP Schiff碱(13)、双对二甲氨基苯甲醛缩BAPP Schiff碱(14)和双丹皮酚缩BAPP Schiff碱(15)]。利用AEP、丹皮酚与水合硝酸铜反应,或BAPP、水杨醛与氯化锌反应分别制得2个Schiff碱铜、锌配合物[丹皮酚缩AEPSchiff碱铜配合物(16)和二水杨醛合双水杨醛缩BAPP Schiff碱双核锌配合物(17)]。分别采用元素分析、红外光谱、核磁共振氢谱和碳谱、紫外光谱、差热-热重等手段对产物进行了表征,并通过单晶X-射线衍射解析了其中6个化合物的晶体结构。利用循环伏安法研究了铜配合物(16)的电化学性质。研究了部分含哌嗪环化合物的抑菌活性、与BSA及CT-DNA的相互作用。
In this paper, eight derivatives of five-or six-membered nitrogen-containing heterocyclic compounds of 1-phenyl-3-methyl-2-pyrazolin-5-one (namely PMP),1-(2-aminoethyl)-piperazine (namely AEP) and 1,4-bis(3-aminopropyl)piperazine (namely BAPP) were synthesized. And with these derivatives used as ligands, nine transition metal complexes were synthesized by classical solution method or solvothermal method. These compounds were characterized by elemental analysis, IR,'H NMR,13C NMR, UV-vis and fluorescent spectrum. The crystal structures of fifteen compounds were determined by single-crystal X-ray diffraction. The thermal stabilities of some compounds were studied by TG-DTA method and their electrochemical properties were also investigated by cyclic voltammetry. Furthermore, the biological activities such as antibacterial activity, interaction with Bovine Serum Albumin (BSA) and calf thymus DNA (CT-DNA) for some compounds were investigated preliminary by the agar diffusion method, electronic absorption spectroscopy and viscometry, respectively.
Five-membered azaheterocyclic ligand PMP was synthesized by the reaction of acetylacetic ester with phenylhydrazine. With PMP used as reactant, two compounds, PMP (1) in enol form and 4,4'-methenyl-bis(1-phenyl-3-methyl-2-pyrazolin-5-one) (2), were obtained respectively under solvothermal condition in the presence of different volume of acetonitrile. Another new compound, Ethylenediammonium bis(5-methyl-3-oxo-2-phenyl-2,3-dihydro-pyrazol-1-ide) (3), was prepared by the reaction of PMP with ethylenediamine in methanol solution. Their structures were confirmed by elemental analysis, IR,'H NMR,13C NMR spectrum, TG-DTA and single-crystal X-ray diffraction analysis.
Four transition metal complexes of PMP were prepared by the reaction of PMP with zinc chloride, zinc acetate hydrate, cadmium chloride hydrate and cadmium acetate hydrate in methanol solution, respectively. And three single crystals of these complexes, [Zn(PMP)2Cl]n (4)、[Cd(PMP)2]n (6) and [Cd2(PMP)2Cl4]n (7), were also obtained. These complexes were characterized by spectral analysis. Their thermal stabilities were studied by TG-DTA method and their electrochemical properties were also investigated by cyclic voltammetry. The biological activities for some PMP complexes were also preliminary studied. The single-crystal X-ray diffraction revealed that complex (4) is 1-D chain coordination polymer, complex (6) 3-D coordination polymer and complex (7) 2-D ladder coordination polymer.
Two complexes, [Zn2(dien)2Cl4] (8) and{[Cu(dien)NO3]NO3}_n(9), were obtained by the reaction of diethylenetriamine with zinc chloride or copper nitrate hydrate, respectively, in the presence of PMP in methanol solution. The structures of the two complexes were confirmed by elemental analysis, IR spectrum and single-crystal X-ray diffraction. Furthermore, their thermal stabilities were studied by TG-DTA method and their electrochemical properties were investigated by cyclic voltammetry.
The solvothermal treatment of the mixture of copper chloride dihydrate and acetonitrile in the presence of 5,5-dimethyl-imidazolidine-2,4-dione (namely DMH) resulted in the formation of a new acetate-bridged dinuclear copper complex, [Cu2Cl2(μ-Ac)4](H3C2ONH)2 (10). The complex was characterized by elemental analysis, IR spectrum and single-crystal X-ray diffraction, and its electrochemical property was also studied by cyclic voltammetry.
A novel polynitrile containing piperazine ring, N,N,N',N'-tetra(2-cyanoethyl)-1,4-bis-(3-aminopropyl)piperazine (11), was synthesized by the nucleophilic addition reaction of BAPP and acrylonitrile for the first time. Compound (11) was characterized by elemental analysis, IR,~1H NMR spectrum and TG-DTA analysis, and its crystal structure was determined by single-crystal X-ray diffraction.
Five Schiff base compounds, bis(p-hydroxylbenzaldehyde)-BAPP (12), bis(salicylal)-BAPP (13), bis(p-dimethylaminobenzaldehyde)-BAPP (14) and bis(paeonol)-BAPP (15), were synthesized by condensation of BAPP with p-hydroxylbenzaldehyde, salicylal, p-dimethylaminobenzaldehyde and paeonol, respectively. And two complexes, copper paeonol-AEP Schiff base complex (16) and dinuclear zinc bis(salicyal)-BAPP Schiff base complex (17), were obtained by the reaction of AEP, paeonol and copper nitrate dihydrate or by the reaction of salicyal, BAPP and zinc chloride, respectively. These compounds were characterized by elemental analysis, spectral analysis and TG-DTA method, and the crystal structures of six compounds were determined by single-crystal X-ray diffraction. The electrochemical behavior of complex (16) was studied by cyclic voltammetry. Moreover, antibacterial activities and interaction with BSA and CT-DNA for some compounds containing piperazine ring were also investigated.
引文
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