多苯并咪唑配合物的合成及其超氧化物歧化酶模拟活性研究
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摘要
多苯并咪唑类化合物的模拟酶活性和配位化学性质引起我们的特别关注和兴趣。本文以多苯并咪唑基为主线从配体合成、配合物合成到SOD模拟活性研究,从晶体结构表征到SOD模拟物消除活性氧物种的机制探讨。本文的研究手段基于常规的方法,目的是探讨多苯并咪唑类化合物与金属配合后的结构特征,对SOD模拟活性的影响。总的来说,我们围绕目标开展研究,小有收获。
1 设计并合成了三个含多苯并咪唑基化合物配体:三(2-苯并咪唑亚甲基)胺(NTB)、N,N,N′,N′-四(2-苯并咪唑亚甲基)-1,2-乙二胺(EDTB)和N,N,N′,N′-四(2-苯并咪唑甲基)-1,4-二乙氨基乙二醚(EGTB),即C_(34)H_(32)N_(10)·2C_2H_6O·2H_2O、C_(34)H_(32)N_(10)·2C_2H_6O_2和C_(38)H_(44)N_(10)O_2·2ClO_4·2Cl·2CH_3OH,分别得到了它们的单晶,通过X-射线衍射测试并解析后发现后两者为新化合物。
2 设计、合成了含多苯并咪唑基的多齿金属配合物单晶七个。解析了这七个配合物的晶体结构,从晶体结构发现:(1) 含三个苯并咪唑环的NTB金属化合物依中心离子不同,有八面体结构,其化合物为“蝴蝶型”,也有三角双锥结构,其化合物呈“齿轮型”;(2) 含四个苯并咪唑环的EDTB金属化合物,由于EDTB的柔性小,其中心离子均为扭曲的八面体结构;(3) 含四个苯并咪唑基由乙二醚基相连的EGTB本身拥有内桥基(-OCH_2CH_2O-),通过内桥、醋酸根和氯阴离子构成三桥双核配合物,镍中心离子为稍有扭曲的八面体几何构型。
X-射线单晶衍射测试、红外、紫外等方法确定了三(2-苯并咪唑亚甲基)胺的Fe(Ⅲ)和Co(Ⅱ)配合物的结构,由晶体结构发现金属配位情况不同、配合物在结构上存在着差异,Fe(Ⅲ)(NTB)为八面体构型,而Co(NTB)为三角双锥构型;其次,两配合物中的苯并咪唑环间夹角不同,配合物中包含N2和N4的两个苯并咪唑环间夹角仅为9.41(0.11),几乎构成一个平面,呈蝴蝶形;后者Co(NTB)三个苯并咪唑环几乎平分了整个空间,它们之间的夹角约为120,呈三扇叶螺旋桨式构型,为齿轮形。
用X-射线单晶衍射测试了EDTB金属配合物的四个单晶,[Cu(C_(34)H_(32)N_(10))CdBr_4·3H_2O]和[Cu(C_(34)H_(32)N_(10))ZnCl_4·4CH_3OH]两个化合物为[Cu(Ⅱ)EDTB]~(2+)阳离子与大阴离子CdBr_4~(2-)或者ZnCl_4~(2-)相结合的溶剂化物,而[Ni(C_(34)H_(32)N_(10))(NO_3)_2·C_2H_5OH]和[Ni(C_(34)H_(32)N_(10))Cl_2·CH_3OH·C_2H_5OH]为EDTB-Ni~(2+)配阳离子与阴离子Cl~-或者NO_3~-相结合的溶剂化物。晶体解析表明EDTB-Cu(Ⅱ)和EDTB-Ni(Ⅱ)配合物中,中心离子分别与四个苯并咪唑氮和两个氨基氮配位,Cu(Ⅱ)
Multi-benzimidazole compounds have attracted great attention by their mimic enzyme activities, such as superoxide dismutase activity, catalase activity, and their coordination chemistry. In this dissertation, we selected multi-benzimidazole compounds as a main ligand to study the structure characteristic of its complexes and their influence on the activity of eliminating active oxygen by means of X-ray single crystal diffractometer, Here are the results.(i) We designed and synthesized multi-benzimidazole compounds, and obtained three single crystals, by means of X-ray single crystal diffraction method, among which three were characterized and two were novel. The novel compound is C34H32N10 2C2H6O2 and C38H44N10O2 2C1O4-2Cl-2CH3OH, i.e. EDTB-2C2H6O2 (EDTB = N,N,N',N'-tetrakis-(2'-benzimidazolylmethyl)-l,2-ethanediamine), and (EGTBH4)-2C1O4-2C1-2CH3OH, (EGTB= N,N,N',N'-tetrakis-(2-benzimidazolyl methyl-1,4-di-ethylene amino) glycol ether).(ii) We designed and synthesized seven metal-containing multi-benzimidazole complexes. All of them were analyzed by X-ray single crystal diffraction method. Crystal structure showed that: (1) NTB metal complexes which contained three benzimidazole group have different coordination geometry according to central metal ion, such as octahedron structure, formed butterfly-like shape complex, and triangle bipyramid structure, gear-like shape compound, respectively. (2) EDTB metal complexes in which contained four benzimidazole groups have distorted octahedron geometry structure because of rigidity of EDTB. (3) EGTB metal complexes in which included four benzimidazole groups and an intra-ligand (-OCH2CH2O-) group have slightly distorted octahedron structure.The structure of [Fe(NTB)Cl2]Cl-CH3OH-2H2O and [Co(NTB)Cl](CoCl4)-CH3OH were confirmed by means of X-ray single crystal diffraction method, IR and UV. Crystal structure showed that [Fe(NTB)Cl2]+ moiety has octahedron geometry and [Co(NTB)Cl]+ moiety has triangle bipyramid configuration. The dihedral angel between the benzimidazole rings is different in the two complexes, in [Fe(NTB)Cl2]+ moiety, the angel
between the two benzimidazole rings including N2 and N4 is 9.41(0.11)° and the two benzimidazole rings is nearly on a plane, butterfly shape complex formed. But in the [Co(NTB)Cl]+ moiety, the three benzimidazole rings shared the whole space equally, the dihedral angel among them is about 120°, just like three fan blades of an airscrew, the molecular structure appear gear-like shape.Four single crystal of metal-containing EDTB complexes were characterized by X-Ray single diffraction method, and crystal structure show that Cu(EDTB)CdBr4-3H2O or Cu(EDTB)ZnCl4-4CH3OH is combined [CuEDTB]2+ cation with large counter ion [CdBr4]2 " or [ZnCl4]2 " , but in the complex Ni(EDTB)Cl2-CH3OH-C2H5OH or Ni(EDTB)(NO3)2-C2H5OH the counter ion is simple ion Cl" or NO3". In the four EDTB metal complexes the central ion is coordinated by four benzimidazole N atoms and two amine N atoms. The coordination geometry around the central ion can be described as distorted octahedron. Anyway, the four complexes are novel compound.The novel dinuclear Ni2+ complex [Ni2(yu-Cl)(//-0Ac)(EGTB)]-Cl-C104-2CH30H is bridged triply bridging agents of a chloride ion, an acetate and an intra-ligand (-OCH2CH2O-) group. The nickel coordination geometry is that of a slightly distorted octahedron with a NiN3O2Cl arrangement of the ligand donor atoms. Each identical Ni(II) cation is coordinated by a chloride ion, an oxygen atom from the acetate, an ether oxygen atom from the ligand and three nitrogen atoms from two benzimidazole groups and an aliphatic amine group of the same ligand. Because of flexibility of EGTB, each identical Ni(II) geometry is slightly distorted octahedron. Whole molecular is highly symmetrical and has particular nest-shape structure.Common ground of multi-benzimidazole metal complex is that the bond distance between benzimidazole N atoms and metal is shorter than the distance between amine group N atom and metal. The different metal-N bond length is likely due to benzimidazole N atoms can provide better o and 71 electron donor than amine group N atom, naturally, the metal ion bond more tightly.(iv) The pyrogallol UV-VIS spectrophotometeric method was performed to study the activity of SOD mimics at 320nm. The Ni(II)(EDTB) cationic species exhibit a high SOD mimic activity, but Cu(II)(EDTB) and [Ni2(EGTB)Cl(OAc)] cationic species do not have SOD mimic activity.
1 设计并合成了三个含多苯并咪唑基化合物配体:三(2-苯并咪唑亚甲基)胺(NTB)、N,N,N′,N′-四(2-苯并咪唑亚甲基)-1,2-乙二胺(EDTB)和N,N,N′,N′-四(2-苯并咪唑甲基)-1,4-二乙氨基乙二醚(EGTB),即C_(34)H_(32)N_(10)·2C_2H_6O·2H_2O、C_(34)H_(32)N_(10)·2C_2H_6O_2和C_(38)H_(44)N_(10)O_2·2ClO_4·2Cl·2CH_3OH,分别得到了它们的单晶,通过X-射线衍射测试并解析后发现后两者为新化合物。
2 设计、合成了含多苯并咪唑基的多齿金属配合物单晶七个。解析了这七个配合物的晶体结构,从晶体结构发现:(1) 含三个苯并咪唑环的NTB金属化合物依中心离子不同,有八面体结构,其化合物为“蝴蝶型”,也有三角双锥结构,其化合物呈“齿轮型”;(2) 含四个苯并咪唑环的EDTB金属化合物,由于EDTB的柔性小,其中心离子均为扭曲的八面体结构;(3) 含四个苯并咪唑基由乙二醚基相连的EGTB本身拥有内桥基(-OCH_2CH_2O-),通过内桥、醋酸根和氯阴离子构成三桥双核配合物,镍中心离子为稍有扭曲的八面体几何构型。
X-射线单晶衍射测试、红外、紫外等方法确定了三(2-苯并咪唑亚甲基)胺的Fe(Ⅲ)和Co(Ⅱ)配合物的结构,由晶体结构发现金属配位情况不同、配合物在结构上存在着差异,Fe(Ⅲ)(NTB)为八面体构型,而Co(NTB)为三角双锥构型;其次,两配合物中的苯并咪唑环间夹角不同,配合物中包含N2和N4的两个苯并咪唑环间夹角仅为9.41(0.11),几乎构成一个平面,呈蝴蝶形;后者Co(NTB)三个苯并咪唑环几乎平分了整个空间,它们之间的夹角约为120,呈三扇叶螺旋桨式构型,为齿轮形。
用X-射线单晶衍射测试了EDTB金属配合物的四个单晶,[Cu(C_(34)H_(32)N_(10))CdBr_4·3H_2O]和[Cu(C_(34)H_(32)N_(10))ZnCl_4·4CH_3OH]两个化合物为[Cu(Ⅱ)EDTB]~(2+)阳离子与大阴离子CdBr_4~(2-)或者ZnCl_4~(2-)相结合的溶剂化物,而[Ni(C_(34)H_(32)N_(10))(NO_3)_2·C_2H_5OH]和[Ni(C_(34)H_(32)N_(10))Cl_2·CH_3OH·C_2H_5OH]为EDTB-Ni~(2+)配阳离子与阴离子Cl~-或者NO_3~-相结合的溶剂化物。晶体解析表明EDTB-Cu(Ⅱ)和EDTB-Ni(Ⅱ)配合物中,中心离子分别与四个苯并咪唑氮和两个氨基氮配位,Cu(Ⅱ)
Multi-benzimidazole compounds have attracted great attention by their mimic enzyme activities, such as superoxide dismutase activity, catalase activity, and their coordination chemistry. In this dissertation, we selected multi-benzimidazole compounds as a main ligand to study the structure characteristic of its complexes and their influence on the activity of eliminating active oxygen by means of X-ray single crystal diffractometer, Here are the results.(i) We designed and synthesized multi-benzimidazole compounds, and obtained three single crystals, by means of X-ray single crystal diffraction method, among which three were characterized and two were novel. The novel compound is C34H32N10 2C2H6O2 and C38H44N10O2 2C1O4-2Cl-2CH3OH, i.e. EDTB-2C2H6O2 (EDTB = N,N,N',N'-tetrakis-(2'-benzimidazolylmethyl)-l,2-ethanediamine), and (EGTBH4)-2C1O4-2C1-2CH3OH, (EGTB= N,N,N',N'-tetrakis-(2-benzimidazolyl methyl-1,4-di-ethylene amino) glycol ether).(ii) We designed and synthesized seven metal-containing multi-benzimidazole complexes. All of them were analyzed by X-ray single crystal diffraction method. Crystal structure showed that: (1) NTB metal complexes which contained three benzimidazole group have different coordination geometry according to central metal ion, such as octahedron structure, formed butterfly-like shape complex, and triangle bipyramid structure, gear-like shape compound, respectively. (2) EDTB metal complexes in which contained four benzimidazole groups have distorted octahedron geometry structure because of rigidity of EDTB. (3) EGTB metal complexes in which included four benzimidazole groups and an intra-ligand (-OCH2CH2O-) group have slightly distorted octahedron structure.The structure of [Fe(NTB)Cl2]Cl-CH3OH-2H2O and [Co(NTB)Cl](CoCl4)-CH3OH were confirmed by means of X-ray single crystal diffraction method, IR and UV. Crystal structure showed that [Fe(NTB)Cl2]+ moiety has octahedron geometry and [Co(NTB)Cl]+ moiety has triangle bipyramid configuration. The dihedral angel between the benzimidazole rings is different in the two complexes, in [Fe(NTB)Cl2]+ moiety, the angel
between the two benzimidazole rings including N2 and N4 is 9.41(0.11)° and the two benzimidazole rings is nearly on a plane, butterfly shape complex formed. But in the [Co(NTB)Cl]+ moiety, the three benzimidazole rings shared the whole space equally, the dihedral angel among them is about 120°, just like three fan blades of an airscrew, the molecular structure appear gear-like shape.Four single crystal of metal-containing EDTB complexes were characterized by X-Ray single diffraction method, and crystal structure show that Cu(EDTB)CdBr4-3H2O or Cu(EDTB)ZnCl4-4CH3OH is combined [CuEDTB]2+ cation with large counter ion [CdBr4]2 " or [ZnCl4]2 " , but in the complex Ni(EDTB)Cl2-CH3OH-C2H5OH or Ni(EDTB)(NO3)2-C2H5OH the counter ion is simple ion Cl" or NO3". In the four EDTB metal complexes the central ion is coordinated by four benzimidazole N atoms and two amine N atoms. The coordination geometry around the central ion can be described as distorted octahedron. Anyway, the four complexes are novel compound.The novel dinuclear Ni2+ complex [Ni2(yu-Cl)(//-0Ac)(EGTB)]-Cl-C104-2CH30H is bridged triply bridging agents of a chloride ion, an acetate and an intra-ligand (-OCH2CH2O-) group. The nickel coordination geometry is that of a slightly distorted octahedron with a NiN3O2Cl arrangement of the ligand donor atoms. Each identical Ni(II) cation is coordinated by a chloride ion, an oxygen atom from the acetate, an ether oxygen atom from the ligand and three nitrogen atoms from two benzimidazole groups and an aliphatic amine group of the same ligand. Because of flexibility of EGTB, each identical Ni(II) geometry is slightly distorted octahedron. Whole molecular is highly symmetrical and has particular nest-shape structure.Common ground of multi-benzimidazole metal complex is that the bond distance between benzimidazole N atoms and metal is shorter than the distance between amine group N atom and metal. The different metal-N bond length is likely due to benzimidazole N atoms can provide better o and 71 electron donor than amine group N atom, naturally, the metal ion bond more tightly.(iv) The pyrogallol UV-VIS spectrophotometeric method was performed to study the activity of SOD mimics at 320nm. The Ni(II)(EDTB) cationic species exhibit a high SOD mimic activity, but Cu(II)(EDTB) and [Ni2(EGTB)Cl(OAc)] cationic species do not have SOD mimic activity.
引文
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