Synthesis, crystal structure, electrochemistry and antioxidative activity of copper(II), manganese(II) and nickel(II) complexes containing bis(N-ethylbenzimidazol-2-ylmethyl)aniline

被引:40
作者
Wu, Huilu [1 ]
Peng, Hongping [1 ]
Zhang, Yanhui [1 ]
Wang, Fei [1 ]
Zhang, Han [1 ]
Wang, Cuiping [1 ]
Yang, Zaihui [1 ]
机构
[1] Lanzhou Jiaotong Univ, Sch Chem & Biol Engn, Lanzhou 730070, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
benzimidazole; transition metal complexes; crystal structure; electrochemical property; antioxidation; DNA-BINDING PROPERTIES; SUPEROXIDE-DISMUTASE ACTIVITY; METAL-ORGANIC FRAMEWORKS; COBALT(II) COMPLEXES; DERIVATIVES; CYTOTOXICITY; DISCRETE; EPR;
D O I
10.1002/aoc.3313
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Bis(N-ethylbenzimidazol-2-ylmethyl)aniline (Etbba) and its transition metal complexes, [Cu(Etbba)(Cl)(2)]DMF (1), [Mn(Etbba)(Cl)(2)] (2) and [Ni(Etbba)(Cl)(2)] (3), have been synthesized and characterized on the basis of elemental analysis, molar conductivity, UV-visible, infrared and NMR spectroscopies and X-ray crystallography. The coordination environment of complex 1 can be described as distorted square-based pyramidal, while complexes 2 and 3 each have a distorted trigonal bipyramidal geometry. Cyclic voltammograms of complex 1 indicate an electrochemically quasi-reversible Cu2+/Cu+ couple. In addition, the antioxidant activities of the free ligand and its complexes were investigated using the superoxide and hydroxyl radical scavenging methods in vitro. Complexes 1, 2, 3 are found to possess potent hydroxyl radical scavenging activity and to be better than standard antioxidants like vitamin C and mannitol. Furthermore, complexes 1 and 2 exhibit significant superoxide radical activity. Copyright (c) 2015 John Wiley & Sons, Ltd.
引用
收藏
页码:443 / 449
页数:7
相关论文
共 41 条
[11]   Synthesis and cytotoxicity evaluation of some benzimidazole-4,7-diones as bioreductive anticancer agents [J].
Gellis, Armand ;
Kovacic, Herve ;
Boufatah, Narimene ;
Vanelle, Patrice .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (09) :1858-1864
[12]   The synthesis and antioxidant activity of the Schiff bases of chitosan and carboxymethyl chitosan [J].
Guo, ZY ;
Xing, RE ;
Liu, S ;
Yu, HH ;
Wang, PB ;
Li, CP ;
Li, PC .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (20) :4600-4603
[13]   Synthesis and antimicrobial activity of some novel phenyl and benzimidazole substituted benzyl ethers [J].
Guven, Ozden Ozel ;
Erdogan, Taner ;
Goker, Hakan ;
Yildiz, Sulhiye .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (08) :2233-2236
[14]   The combinatorial synthesis of bicyclic privileged structures or privileged substructures [J].
Horton, DA ;
Bourne, GT ;
Smythe, ML .
CHEMICAL REVIEWS, 2003, 103 (03) :893-930
[15]   Ligand-directed strategy for zeolite-type metal-organic frameworks: Zinc(II) imidazolates with unusual zeolitic topologies [J].
Huang, XC ;
Lin, YY ;
Zhang, JP ;
Chen, XM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (10) :1557-1559
[16]   Manganese complexes displaying superoxide dismutase activity: A balance between different factors [J].
Iranzo, Olga .
BIOORGANIC CHEMISTRY, 2011, 39 (1-3) :73-87
[17]   Synthesis and activity of 1H-benzimidazole and 1H-benzotriazole derivatives as inhibitors of Acanthamoeba castellanii [J].
Kopanska, K ;
Najda, A ;
Zebrowska, J ;
Chomicz, L ;
Piekarczyk, J ;
Myjak, P ;
Bretner, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (10) :2617-2624
[18]   Synthesis, structure and SOD-like activity of a ternary Cu(II) complex with 1,10-phenanthroline and L-valinate [J].
Le, Xueyi ;
Liao, Shenrong ;
Liu, Xiaopin ;
Feng, Xiaolong .
JOURNAL OF COORDINATION CHEMISTRY, 2006, 59 (09) :985-995
[19]   Self-assembly of discrete cyclic nanostructures mediated by transition metals [J].
Leininger, S ;
Olenyuk, B ;
Stang, PJ .
CHEMICAL REVIEWS, 2000, 100 (03) :853-907
[20]   Synthesis, characterization, antioxidant activity and DNA-binding studies of two rare earth(III) complexes with naringenin-2-hydroxy benzoyl hydrazone ligand [J].
Li, Tian-Rong ;
Yang, Zheng-Yin ;
Wang, Bao-Dui ;
Qin, Dong-Dong .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (08) :1688-1695