Synthesis, thermal, spectral, antimicrobial and cytotoxicity profile of the Schiff bases bearing pyrazolone moiety and their Cu(II) complexes

被引：0
作者：
Irina Zarafu
Rodica Olar
Mariana Carmen Chifiriuc
Coralia Bleotu
Petre Ioniţă
Mihaela Mulţescu
Gabriela Ioniţă
Graţiela Grădişteanu
Arnaud Tatibouët
Mihaela Badea
机构：
[1] University of Bucharest,Department of Organic Chemistry, Faculty of Chemistry
[2] University of Bucharest,Department of Inorganic Chemistry, Faculty of Chemistry
[3] University of Bucharest,Department of Microbiology, Faculty of Biology
[4] ICUB,The Research Institute of the University of Bucharest
[5] Stefan S Nicolau Institute of Virology,ICOA
[6] Romanian Academy,UMR7311, CNRS
[7] “Ilie Murgulescu” Physical Chemistry Institute,undefined
[8] University of Orleans,undefined
来源：
Journal of Thermal Analysis and Calorimetry | 2018年 / 134卷
关键词：
4-Aminoantipyrine; Copper complex; Biofilm; Cytotoxicity; Schiff base; Thermal behaviour;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A series of Schiff bases resulted in the [1 + 1] condensation of 8-alkyl-2-hydroxy-tricyclo[7.3.1.02.7]-tridecan-13-one with the 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one, and their complexes CuL(CH3COO)2·nH2O were synthesized. The compounds were characterized by microanalytical, ESI–MS, NMR, IR, electronic and EPR spectra. Based on the ESI–MS and IR spectra, a mononuclear structure with both Schiff base and acetate as chelate was proposed for complexes. An elongated rhombic stereochemistry was assigned considering electronic and EPR data. The thermal analyses have evidenced processes as water elimination, acetate decomposition as well as oxidative degradation of the Schiff base moiety. The bioevaluation of compounds in relation to planktonic and biofilm-embedded microbial cells, as well as to human cells, indicates an improved activity of complexes over ligands. The same tendency was observed for antioxidant activity.
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页码：1851 / 1861
页数：10
相关论文
共 245 条
[1]  
Casas JS(2007)Coordination modes of 5-pyrazolones: a solid-state overview Coord Chem Rev 251 1561-1589
[2]  
García-Tasende MS(2014)Design, synthesis and the biological evaluation of new 1,3-thiazolidine-4-ones based on the 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one scaffold Molecules 19 13824-13847
[3]  
Sánchez A(2010)Synthesis and biological evaluation of Eur J Med Chem 45 4761-4768
[4]  
Sordo J(2017)-antipyrine-4-substituted amino-3-chloromaleimide derivatives Eur J Med Chem 141 603-614
[5]  
Touceda A(2017)Synthesis, antitumor evaluation and microarray study of some new pyrazolo[3,4-d][1,2,3]triazine derivatives Interdiscip Sci Comput Life Sci 9 130-139
[6]  
Apotrosoaei M(2017)Design, synthesis, spectral analysis, in vitro anticancer evaluation and molecular docking studies of some fluorescent 4-amino-2, 3-dimethyl-1-phenyl-3-pyrazolin-5-one, ampyrone derivatives Med Chem Res 26 1969-1987
[7]  
Vasincu IM(2018)Design, synthesis and QSAR studies of 2-amino benzo[d]thiazolyl substituted pyrazol-5-ones: novel class of promising antibacterial agents J Mol Liq 252 329-338
[8]  
Dragan M(2010)Pyrazole, pyrazolone and enaminonitrile pyrazole derivatives: Synthesis, characterization and potential in corrosion inhibition and antimicrobial applications Eur J Med Chem 45 2258-2264
[9]  
Buron F(2016)Scavenging activity of aminoantipyrines against hydroxyl radical Synth Commun 46 1567-1594
[10]  
Routier S(2016)Chemistry of antipyrine Curr Top Med Chem 16 3569-3581
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