Quinolin-2(1H)-one-triazole derived Schiff bases and their Cu(II) and Zn(II) complexes: possible new therapeutic agents

被引:78
作者
Creaven, Bernadette S. [1 ,2 ]
Devereux, Michael [3 ]
Foltyn, Agnieszka [1 ,2 ]
McClean, Siobhan [1 ,2 ]
Rosair, Georgina [4 ]
Thangella, Venkat Reddy [1 ,2 ]
Walsh, Maureen [1 ,2 ]
机构
[1] Inst Technol Tallaght, Dept Sci, Dublin 24, Ireland
[2] Inst Technol Tallaght, Ctr Appl Sci & Hlth, Dublin 24, Ireland
[3] Dublin Inst Technol, Focas Inst, Inorgan Pharmaceut & Biomimet Res Grp, Dublin 2, Ireland
[4] Heriot Watt Univ, Sch Engn & Phys Sci, Edinburgh EH14 4AS, Midlothian, Scotland
关键词
Quinolin-2(1H)-one; 4-Amino-1,2,4-triazole; Schiff bases; Metal(II) complexes; Biological activity; X-ray structures; TRANSITION-METAL-COMPLEXES; RAY CRYSTAL-STRUCTURES; ONE-POT SYNTHESIS; COPPER(II) COMPLEXES; ANTIMICROBIAL ACTIVITY; SPECTROSCOPIC CHARACTERIZATION; ANTIBACTERIAL ACTIVITY; BIOLOGICAL-ACTIVITY; ANTICANCER ACTIVITY; ZINC(II) COMPLEXES;
D O I
10.1016/j.poly.2009.11.002
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The condensation of 4-amino-1,2,4-triazole with N-substituted-3-formyl-4-hydroxyquinolin-2-(1H)-one derivatives has lead to the synthesis of a new series of quinolin-2(1H)-one-triazole derived Schiff base ligands (1-3). Cu(II) and Zn(II) complexes (1a-3a and 1b-3b, respectively) of these ligands were also prepared. The complexes were characterised by standard techniques and for two of the complexes X-ray crystallography confirmed that the geometry at the metal centre was octahedral in both cases and that the Schiff base acted as a bidentate ligand coordinating to the metal(II) ion through the deprotonated oxygen and azomethine nitrogen atoms. All of the compounds were investigated for their antimicrobial activities against a fungal strain, Candida albicans, and against Gram-positive and Gram-negative bacteria. The compounds were found to be active against C. albicans but inactive against Staphylococcus aureus and Escherichia coli. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:813 / 822
页数:10
相关论文
共 66 条
[1]  
Abass M, 2000, CHEM PAP-CHEM ZVESTI, V54, P187
[2]  
[Anonymous], 2004, APEX2
[3]   Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases [J].
Bagihalli, Gangadhar B. ;
Avaji, Prakash Gouda ;
Patil, Sangamesh A. ;
Badami, Prema S. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (12) :2639-2649
[4]   Synthesis, characterization and cytotoxicity evaluation of some new platinum(II) complexes of tetrazolo[1,5-a]quinolines [J].
Bekhit, AA ;
El-Sayed, OA ;
Al-Allaf, TAK ;
Aboul-Enein, HY ;
Kunhi, M ;
Pulicat, SM ;
Al-Hussain, K ;
Al-Khodairy, F ;
Arif, J .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (06) :499-505
[5]  
Bhudevi B, 2009, INDIAN J CHEM B, V48, P255
[6]   Metal-assisted syntheses and NMR characterization of square-planar Pd(II) and Pt(II) complexes with tridentate nitrogen-donor chelate ligands [J].
Bortoluzzi, Marco ;
Paolucci, Gino ;
Pitteri, Bruno ;
Vavasori, Andrea .
INORGANIC CHEMISTRY COMMUNICATIONS, 2006, 9 (12) :1301-1303
[7]   Update on antifungal drug resistance mechanisms of Aspergillus fumigatus [J].
Chamilos, G ;
Kontoyiannis, DP .
DRUG RESISTANCE UPDATES, 2005, 8 (06) :344-358
[8]   Modern spectroscopic techniques in the characterization of Schiff base macrocyclic ligand and its complexes with transition metals [J].
Chandra, S ;
Gupta, LK .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2005, 62 (1-3) :307-312
[9]  
Cotton A. F., 1999, ADV INORG CHEM, V6th
[10]   Synthesis, characterisation and antimicrobial activity of copper(II) and manganese(II) complexes of coumarin-6,7-dioxyacetic acid (cdoaH2) and 4-methylcoumarin-6,7-dioxyacetic acid (4-MecdoaH2):: X-ray crystal structures of [Cu(cdoa)(phen)2] • 8.8H2O and [Cu(4-Mecdoa)(phen)2] • 13H2O (phen=1,10-phenanthroline) [J].
Creaven, Bernadette S. ;
Egan, Denise A. ;
Karcz, Dariusz ;
Kavanagh, Kevin ;
McCann, Malachy ;
Mahon, Mary ;
Noble, Andy ;
Thati, Bhumika ;
Walsh, Maureen .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2007, 101 (08) :1108-1119