Schiff碱金属配合物的合成及其抗菌活性研究进展
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摘要
介绍了Schiff碱金属配合物的直接合成法、分步合成法、模板合成法、逐滴反应法、高度稀释法以及水热合成法等,综述了Ni(Ⅱ)、Cu(Ⅱ)、Co(Ⅱ)、Zr(Ⅱ)等过渡金属以及Nd(Ⅲ)、Sm(Ⅲ)等稀土金属等形成的Schiff碱金属配合物结构及其对大肠杆菌、金黄色葡萄球菌、枯草杆菌等多种细菌的抑制作用。讨论了Schiff碱金属配合物分子设计和应用中尚存的问题,对于新型抗菌药物的研发有一定的借鉴意义。
The direct synthesis,stepwise synthesis,template synthesis,drop-by-drop reaction,highly dilute and hydrothermal synthesis of Schiff base metal complexes were introduced. The structure of Schiff-base metal complexes formed by transition metals( Ni( Ⅱ) 、Cu( Ⅱ) 、Co( Ⅱ) 、Zr( Ⅱ),etc.)and rare earth metals( Nd( Ⅲ),Sm( Ⅲ),etc.) and their antibacterial effects on E. coli,S. aureus,B. subtilis,etc. were reviewed. The problems existing in the molecular design and application of Schiff base metal complexes are discussed,which can be used as a reference for the research and development of new antimicrobial agents.
The direct synthesis,stepwise synthesis,template synthesis,drop-by-drop reaction,highly dilute and hydrothermal synthesis of Schiff base metal complexes were introduced. The structure of Schiff-base metal complexes formed by transition metals( Ni( Ⅱ) 、Cu( Ⅱ) 、Co( Ⅱ) 、Zr( Ⅱ),etc.)and rare earth metals( Nd( Ⅲ),Sm( Ⅲ),etc.) and their antibacterial effects on E. coli,S. aureus,B. subtilis,etc. were reviewed. The problems existing in the molecular design and application of Schiff base metal complexes are discussed,which can be used as a reference for the research and development of new antimicrobial agents.
引文
[1] BARTYZEL A. Synthesis,crystal structure and characterization of manganese(III)complex containing a tetradentate Schiff base[J]. Journal of Coordination Chemistry,2013,66:4292-4303.
[2] RAJPUT J D,BAGUL S D,TADAVI S K,et al.Comparative anti-proliferative studies of natural phenolic monoterpenoids on human malignant tumour cells[J]. Medicinal and Aromatic Plants(Los Angel),2016,5:2167-0412.
[3] DING L Q,ZHANG Y L,CHEN X L,et al. Ni2+-template mechanism to the nonsymmetrical salen-type Schiff-base Ni2+complex with effective catalysis on styrene polymerization[J]. Inorganic Chemistry Communications,2017,76:100-102.
[4] MATSUMOTO K,SAITO B,KATSUKI T. Asymmetric catalysts of metal complexes with non-planar ONNO ligands:Salen,salaen and salan[J]. Chemical Communications,2007,35:3619-3627.
[5] AHMADI M,MAGUE J T,AKBARI A,et al. Dianion N1,N4-bis(salicylidene)-S-allyl-thiosemicarbazide complexes:Synthesis,structure,spectroscopy and thermal behavior[J]. Polyhedron,2012,42:128-134.
[6] YOU J S,SHAO M Y,GAU H M. Enantioselective addition of diethylzinc to aldehydes catalyzed by titanium(IV)complexes of N-sulfonylated amino alcohols with two stereogenic centers[J]. Tetrahedron:Asymmetry,2001,12(21):2971-2975.
[7] QIN W,LONG S,PANUNZIO M,et al. Schiff bases:A short survey on an evergreen chemistry tool[J]. Molecules,2013,18:12264-89.
[8] YOSHINO T,MORIMOTO H,LU G,et al. Magnesium Schiff base catalyzed direct asymmetric aldol reaction[J]. Synfacts,2010,(3):0321-0321.
[9] RAKHTSHAH J,SALEHZADEH S,ZOLFIGOL M A,et al. Mn(III)-pentadentate Schiff base complex supported on multi-walled carbon nanotubes as a green,mild and heterogeneous catalyst for the synthesis of tetrahydrobenzo[b]pyrans via tandem Knoevenagel-Michael cyclocondensation reaction[J]. Applied Organometallic Chemistry,2017,31(9):1-10.
[10] DING L Q,CHU Z,CHEN L L. et al. Pd-Salen and Pd-Salan complexes:Characterization and application in styrene polymerization[J]. Inorganic Chemistry Communications,2011,14:573-577.
[11]刘平,刘岩,马晓伟,等.新型水溶性希夫碱化合物的合成[J].石河子大学学报:自然科学版,2015,33(1):7-10.
[12]李耀昕.杂环类配体及其Ni(II)、Co(III)、Cu(II)希夫碱配合物的合成、结构与性质研究[D].兰州交通大学,2016.
[13] SAVITHRI K,KUMAR B C V,VIVEK H K,et al.Synthesis and characterization of cobalt(III)and copper(II)complexes of 2-((E)-(6-fluorobenzo[d]thiazol-2-ylimino)methyl)-4-chlorophenol:DNA binding and nuclease studies—SOD and antimicrobial activities[J]. International Journal of Spectroscopy,2018,(1):1-15.
[14] THOMAS P S,MOHANAN K. Synthesis and biological evaluation of some 3d metal complexes with a novel heterocyclic Schiff base[J]. Journal of the Chinese Chemical Society,2017,64(12):1510-1523.
[15] COZZI P G. Metal-Salen Schiff base complexes in catalysis:Practical aspects[J]. Chemical Society Reviews,2004,33:410-421.
[16]姚克敏,李冬成,沈联芳,等.镧系与邻氨基苯甲酸型Schiff碱配合物的合成、表征及催化活性[J].化学学报,1993,51:677-682.
[17]李群,杨蕊,赵昔慧.逐滴一步反应法合成L-赖氨酸缩香兰素Schiff碱铜配合物及其表征[J].郑州大学学报(工学版),2008,29(2):120-122.
[18]张鹏飞.吲哚-2,3二酮类希夫碱配合物的合成、表征与生物活性研究[D].青岛:中国海洋大学,2014.
[19] VANCE A L,ALCOCK N W,BUSCH D H,et al.Copper(II)template synthesis of a 20-membered[1+1] schiff base macrocycle and nickel(II)template synthesis of a 40-membered[2+2] schiff base macrocycle from 2,6-pyridinedicarboxaldehyde and 1,13-diamino-4,7,10-trioxatridecane[J]. Inorganic Chemistry,1997,36(22):5132-5134.
[20]谢晶晶.基于新型希夫碱配体的配合物的合成及结构研究[D].长春:东北师范大学,2017.
[21] SHI Q,YANG J X,L X Q. A tetranuclear[Zn4(L)2(OAc)3(OH)] complex based on the Salentype Schiff-base ligand H2L for effective bulk solventfree melt ring-openingpolymerization(ROP)of L-lactide[J]. Inorganic Chemistry Communications,2015,59:61-62.
[22] DING L Q,LIANG S R,ZHANG J T,et al. Cu2+-templated self-assembly of an asymmetric Salen-Cu(II)complex and its application in catalytic polymerization of methyl methacrylate(MMA)[J]. Inorganic Chemistry Communications,2014,44:173-176.
[23] TANAKA K,SHIMOUR R,CAIRA M R. Synthesis,crystal structures and photochromic properties of novel chiral Schiff base macrocycles[J]. Tetrahedron Letters,2010,51(2):449-452.
[24]陈振锋,唐云志,石少明.双核钒希夫碱配合物[VO(μ-OCH3)(Salen)]2合成、表征及晶体结构[J].合成化学,2004,12(5):465-467.
[25]袁琦,赵辉,张淑华.三核铜配合物[Cu3(μ2–dppm)3(μ3-I)2]I的合成和晶体结构研究[J].河南大学学报,2005,35(4):45-48.
[26] SOBOLA A O,WATKINS G M. Complexes of Schiff bases derived from o-aminophenol and salicylaldehyde derivatives[J]. Research on Chemical Intermediates,2013,5:147-154.
[27] SAHRAEI A,KARGAR H,HAKIMI M,et al. Synthesis,characterization,crystal structures and biological activities of eight-coordinate zirconium(IV)Schiff base complexes[J]. Transit Met Chem,2017,42:483-489.
[28] AZIZ M R. Synthesis and antibacterial study of the ligand type Schiff base derived from amino acid[LPhenylalanine] and its complexes with Co(II),Ni(II),Cu(II)and Zn(II)ions[J]. Ibn Al-Haitham Journal for Pure and Applied Science,2010,23(2):???.
[29] KHAN S A,NAMI S A A,BHAT S A,et al. Synthesis,characterization and antimicrobial study of polymeric transition metal complexes of Mn(II),Co(II),Ni(II),Cu(II)and Zn(II)[J]. Microbial Pathogenesis,2017,110:414-425.
[30] TADAVI S K,YADAV A A,BENDRE R S. Synthesis and characterization of a novel Schiff base of 1,2-diaminopropane with substituted salicyaldehyde and its transition metal complexes:Single crystal structures and biological activities[J]. Journal of Molecular Structure,2018,1152:223-231.
[31] TADAVI S K,RAJPUT T D,BAGUL S D. Synthesis,crystal structures,biological screening and electrochemical analysis of some salen-based transition metal complexes[J]. Res Chem Intermed,2017,43:4863-4879.
[32] LIUH Y. Synthesis,structural characterization,and antibacterial activity of Cu(II)and Zn(II)complexes with tetradentate Schiff bases[J]. Synthesis and Reactivity in Inorganic,Metal-Organic,and Nano-Metal Chemistry,2016,46:210-215.
[33] BHARATI KT,GUJARATHI DB,TRYAMBAKE PT,et al. Preparation of Schiff base of 1,2,4-triazole-4-amine with 3-nitrobenzaldehyde,its complexation with Cu(II)and Zn(II)and antimicrobial activity of complexes[J]. Der Chemica Sinica,2017,8(2):223-228.
[34] XU Y,XUE L,WANG Z G. Synthesis,X-ray crystal structures,and antibacterial activities of Schiff base Nickel(II)complexes with similar tetradentate Schiff bases[J]. Russian Journal of Coordination Chemistry,2017,43(5):314-319.
[35] MAJUMDAR D,DAS S,BISWAS J K,et al. Synthesis,structure,fluorescent property,and antibacterial activity of new Cd(II)metal complex based on multidentate Schiff base ligand N,N'-bis(3-methoxysalicylidenimino)-1,3-diaminopropane[J]. Journal of Molecular Structure,2017,1134:617-624.
[36]胡学雷,孟美娜,姜治平,等.双臂大环稀土配合物的合成及其生物活性[J].武汉工程大学学报,2014,36(4):12-16.
[37]李锦州,蒋礼,安郁美.酰基吡唑啉酮缩氨基酸Schiff碱的合成及与稀土配位性能和生物活性研究[J].中国稀土学报,2004,22(2):189-192
[38] CHU L F,SHI Y,XU D F,et al. Synthesis and biological studies of some lanthanide complexes of Schiff base[J]. Synthesis and Reactivity in Inorganic,Metal-Organic,and Nano-Metal Chemistry,2015,45:1617-1626.
[39] AIN Q,PANDEY S K,PANDEY O P,et al. Synthesis,structural characterization and biological studies of neodymium(III)and samarium(III)complexes with mercaptotriazole Schiff bases[J]. Applied Organometallic Chemistry,2016,30:102-108.
[40] MISHRA N,POONIA K,SONI S K,et al. Synthesis,characterization and antimicrobial activity of Schiff base Ce(III)complexes[J]. Polyhedron,2016,120:60-68.
[41] SAKIYAN I,LOGOGLU E,ARSLAN S,et al. Antimicrobial activities of N-(2-hydroxy-1-naphthalidene)-amino acid(glycine,alanine,phenylalanine,histidine,tryptophane)Schiff bases and their manganese(III)complexes[J]. Biometals,2004,17(2):115-120.
[42] MATSUMOTO K,SAITO B,KATSUKI T. Asymmetric catalysts of metal complexes with non-planar ONNO ligands:Salen,salalen and salan[J]. Chemical Communications,2007,35:3619-3627.
[43] KLEIJ A W. Nonsymmetrical salen ligands and their complexes:Synthesis and applications[J]. European Journal of Inorganic Chemistry,2009,2:193-205.
[2] RAJPUT J D,BAGUL S D,TADAVI S K,et al.Comparative anti-proliferative studies of natural phenolic monoterpenoids on human malignant tumour cells[J]. Medicinal and Aromatic Plants(Los Angel),2016,5:2167-0412.
[3] DING L Q,ZHANG Y L,CHEN X L,et al. Ni2+-template mechanism to the nonsymmetrical salen-type Schiff-base Ni2+complex with effective catalysis on styrene polymerization[J]. Inorganic Chemistry Communications,2017,76:100-102.
[4] MATSUMOTO K,SAITO B,KATSUKI T. Asymmetric catalysts of metal complexes with non-planar ONNO ligands:Salen,salaen and salan[J]. Chemical Communications,2007,35:3619-3627.
[5] AHMADI M,MAGUE J T,AKBARI A,et al. Dianion N1,N4-bis(salicylidene)-S-allyl-thiosemicarbazide complexes:Synthesis,structure,spectroscopy and thermal behavior[J]. Polyhedron,2012,42:128-134.
[6] YOU J S,SHAO M Y,GAU H M. Enantioselective addition of diethylzinc to aldehydes catalyzed by titanium(IV)complexes of N-sulfonylated amino alcohols with two stereogenic centers[J]. Tetrahedron:Asymmetry,2001,12(21):2971-2975.
[7] QIN W,LONG S,PANUNZIO M,et al. Schiff bases:A short survey on an evergreen chemistry tool[J]. Molecules,2013,18:12264-89.
[8] YOSHINO T,MORIMOTO H,LU G,et al. Magnesium Schiff base catalyzed direct asymmetric aldol reaction[J]. Synfacts,2010,(3):0321-0321.
[9] RAKHTSHAH J,SALEHZADEH S,ZOLFIGOL M A,et al. Mn(III)-pentadentate Schiff base complex supported on multi-walled carbon nanotubes as a green,mild and heterogeneous catalyst for the synthesis of tetrahydrobenzo[b]pyrans via tandem Knoevenagel-Michael cyclocondensation reaction[J]. Applied Organometallic Chemistry,2017,31(9):1-10.
[10] DING L Q,CHU Z,CHEN L L. et al. Pd-Salen and Pd-Salan complexes:Characterization and application in styrene polymerization[J]. Inorganic Chemistry Communications,2011,14:573-577.
[11]刘平,刘岩,马晓伟,等.新型水溶性希夫碱化合物的合成[J].石河子大学学报:自然科学版,2015,33(1):7-10.
[12]李耀昕.杂环类配体及其Ni(II)、Co(III)、Cu(II)希夫碱配合物的合成、结构与性质研究[D].兰州交通大学,2016.
[13] SAVITHRI K,KUMAR B C V,VIVEK H K,et al.Synthesis and characterization of cobalt(III)and copper(II)complexes of 2-((E)-(6-fluorobenzo[d]thiazol-2-ylimino)methyl)-4-chlorophenol:DNA binding and nuclease studies—SOD and antimicrobial activities[J]. International Journal of Spectroscopy,2018,(1):1-15.
[14] THOMAS P S,MOHANAN K. Synthesis and biological evaluation of some 3d metal complexes with a novel heterocyclic Schiff base[J]. Journal of the Chinese Chemical Society,2017,64(12):1510-1523.
[15] COZZI P G. Metal-Salen Schiff base complexes in catalysis:Practical aspects[J]. Chemical Society Reviews,2004,33:410-421.
[16]姚克敏,李冬成,沈联芳,等.镧系与邻氨基苯甲酸型Schiff碱配合物的合成、表征及催化活性[J].化学学报,1993,51:677-682.
[17]李群,杨蕊,赵昔慧.逐滴一步反应法合成L-赖氨酸缩香兰素Schiff碱铜配合物及其表征[J].郑州大学学报(工学版),2008,29(2):120-122.
[18]张鹏飞.吲哚-2,3二酮类希夫碱配合物的合成、表征与生物活性研究[D].青岛:中国海洋大学,2014.
[19] VANCE A L,ALCOCK N W,BUSCH D H,et al.Copper(II)template synthesis of a 20-membered[1+1] schiff base macrocycle and nickel(II)template synthesis of a 40-membered[2+2] schiff base macrocycle from 2,6-pyridinedicarboxaldehyde and 1,13-diamino-4,7,10-trioxatridecane[J]. Inorganic Chemistry,1997,36(22):5132-5134.
[20]谢晶晶.基于新型希夫碱配体的配合物的合成及结构研究[D].长春:东北师范大学,2017.
[21] SHI Q,YANG J X,L X Q. A tetranuclear[Zn4(L)2(OAc)3(OH)] complex based on the Salentype Schiff-base ligand H2L for effective bulk solventfree melt ring-openingpolymerization(ROP)of L-lactide[J]. Inorganic Chemistry Communications,2015,59:61-62.
[22] DING L Q,LIANG S R,ZHANG J T,et al. Cu2+-templated self-assembly of an asymmetric Salen-Cu(II)complex and its application in catalytic polymerization of methyl methacrylate(MMA)[J]. Inorganic Chemistry Communications,2014,44:173-176.
[23] TANAKA K,SHIMOUR R,CAIRA M R. Synthesis,crystal structures and photochromic properties of novel chiral Schiff base macrocycles[J]. Tetrahedron Letters,2010,51(2):449-452.
[24]陈振锋,唐云志,石少明.双核钒希夫碱配合物[VO(μ-OCH3)(Salen)]2合成、表征及晶体结构[J].合成化学,2004,12(5):465-467.
[25]袁琦,赵辉,张淑华.三核铜配合物[Cu3(μ2–dppm)3(μ3-I)2]I的合成和晶体结构研究[J].河南大学学报,2005,35(4):45-48.
[26] SOBOLA A O,WATKINS G M. Complexes of Schiff bases derived from o-aminophenol and salicylaldehyde derivatives[J]. Research on Chemical Intermediates,2013,5:147-154.
[27] SAHRAEI A,KARGAR H,HAKIMI M,et al. Synthesis,characterization,crystal structures and biological activities of eight-coordinate zirconium(IV)Schiff base complexes[J]. Transit Met Chem,2017,42:483-489.
[28] AZIZ M R. Synthesis and antibacterial study of the ligand type Schiff base derived from amino acid[LPhenylalanine] and its complexes with Co(II),Ni(II),Cu(II)and Zn(II)ions[J]. Ibn Al-Haitham Journal for Pure and Applied Science,2010,23(2):???.
[29] KHAN S A,NAMI S A A,BHAT S A,et al. Synthesis,characterization and antimicrobial study of polymeric transition metal complexes of Mn(II),Co(II),Ni(II),Cu(II)and Zn(II)[J]. Microbial Pathogenesis,2017,110:414-425.
[30] TADAVI S K,YADAV A A,BENDRE R S. Synthesis and characterization of a novel Schiff base of 1,2-diaminopropane with substituted salicyaldehyde and its transition metal complexes:Single crystal structures and biological activities[J]. Journal of Molecular Structure,2018,1152:223-231.
[31] TADAVI S K,RAJPUT T D,BAGUL S D. Synthesis,crystal structures,biological screening and electrochemical analysis of some salen-based transition metal complexes[J]. Res Chem Intermed,2017,43:4863-4879.
[32] LIUH Y. Synthesis,structural characterization,and antibacterial activity of Cu(II)and Zn(II)complexes with tetradentate Schiff bases[J]. Synthesis and Reactivity in Inorganic,Metal-Organic,and Nano-Metal Chemistry,2016,46:210-215.
[33] BHARATI KT,GUJARATHI DB,TRYAMBAKE PT,et al. Preparation of Schiff base of 1,2,4-triazole-4-amine with 3-nitrobenzaldehyde,its complexation with Cu(II)and Zn(II)and antimicrobial activity of complexes[J]. Der Chemica Sinica,2017,8(2):223-228.
[34] XU Y,XUE L,WANG Z G. Synthesis,X-ray crystal structures,and antibacterial activities of Schiff base Nickel(II)complexes with similar tetradentate Schiff bases[J]. Russian Journal of Coordination Chemistry,2017,43(5):314-319.
[35] MAJUMDAR D,DAS S,BISWAS J K,et al. Synthesis,structure,fluorescent property,and antibacterial activity of new Cd(II)metal complex based on multidentate Schiff base ligand N,N'-bis(3-methoxysalicylidenimino)-1,3-diaminopropane[J]. Journal of Molecular Structure,2017,1134:617-624.
[36]胡学雷,孟美娜,姜治平,等.双臂大环稀土配合物的合成及其生物活性[J].武汉工程大学学报,2014,36(4):12-16.
[37]李锦州,蒋礼,安郁美.酰基吡唑啉酮缩氨基酸Schiff碱的合成及与稀土配位性能和生物活性研究[J].中国稀土学报,2004,22(2):189-192
[38] CHU L F,SHI Y,XU D F,et al. Synthesis and biological studies of some lanthanide complexes of Schiff base[J]. Synthesis and Reactivity in Inorganic,Metal-Organic,and Nano-Metal Chemistry,2015,45:1617-1626.
[39] AIN Q,PANDEY S K,PANDEY O P,et al. Synthesis,structural characterization and biological studies of neodymium(III)and samarium(III)complexes with mercaptotriazole Schiff bases[J]. Applied Organometallic Chemistry,2016,30:102-108.
[40] MISHRA N,POONIA K,SONI S K,et al. Synthesis,characterization and antimicrobial activity of Schiff base Ce(III)complexes[J]. Polyhedron,2016,120:60-68.
[41] SAKIYAN I,LOGOGLU E,ARSLAN S,et al. Antimicrobial activities of N-(2-hydroxy-1-naphthalidene)-amino acid(glycine,alanine,phenylalanine,histidine,tryptophane)Schiff bases and their manganese(III)complexes[J]. Biometals,2004,17(2):115-120.
[42] MATSUMOTO K,SAITO B,KATSUKI T. Asymmetric catalysts of metal complexes with non-planar ONNO ligands:Salen,salalen and salan[J]. Chemical Communications,2007,35:3619-3627.
[43] KLEIJ A W. Nonsymmetrical salen ligands and their complexes:Synthesis and applications[J]. European Journal of Inorganic Chemistry,2009,2:193-205.