Chalcone-derived thiosemicarbazones and their zinc(II) and gallium(III) complexes: spectral studies and antimicrobial activity

被引：24

作者：

Da Silva, Jeferson G. ^{[1
]}

Perdigao, Camila C. H. ^{[1
]}

Speziali, Nivaldo L. ^{[2
]}

Beraldo, Heloisa ^{[1
]}

机构：

[1] Univ Fed Minas Gerais, Dept Quim, Belo Horizonte, MG, Brazil

[2] Univ Fed Minas Gerais, Dept Fis, BR-30161 Belo Horizonte, MG, Brazil

来源：

JOURNAL OF COORDINATION CHEMISTRY | 2013年 / 66卷 / 03期

关键词：

Chalcones; Thiosemicarbazone; Zinc(II) complexes; Gallium(III) complexes; Antimicrobial; METAL-COMPLEXES; ANTIFUNGAL ACTIVITY; CYTOTOXIC ACTIVITY; SALICYLALDEHYDE; NLO;

D O I：

10.1080/00958972.2012.757762

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chalcone-derived 3-phenyl-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCTPh) (1), 3-(4-chlorophenyl)-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCT4ClPh) (2), 3-(4-bromophenyl)-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCT4BrPh) (3), and 3-(4-nitrophenyl-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCT4NO2Ph) (4) were obtained as well as their gallium(III) and zinc(II) complexes [Ga(PyCTPh)2]NO3 (Ga1), [Ga(PyCT4ClPh)2]NO3 (Ga2), [Ga(PyCT4BrPh)2]NO3 (Ga3), [Ga(PyCT4NO2Ph)2]NO3 (Ga4), [Zn(PyCTPh)2] (Zn1), [Zn(PyCT4ClPh)2] (Zn2), [Zn(PyCT4BrPh)2] (Zn3), and [Zn(PyCT4NO2Ph)2] (Zn4). The chalcones, thiosemicarbazones, and zinc(II) complexes were not active against Pseudomonas aeruginosa. The thiosemicarbazones proved to be more active than the parent chalcones against Staphylococcus aureus and Candida albicans. Coordination to zinc(II) resulted in activity improvement of most thiosemicarbazones against S. aureus. Coordination to gallium(III) significantly improved the antimicrobial activity of all thiosemicarbazones against the studied micro-organisms, suggesting this to be an effective strategy for antimicrobial activity enhancement.

引用

页码：385 / 401

页数：17

共 43 条

[1] Synthesis, molecular modeling, thermal and spectral studies of metal complexes of hydrazone derived from 5-acetyl-4-hydroxy-2H-1,3-thiazine-2,6(3H)-dione and thiosemicarbazide [J].

Adly, Omima M. I. .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2011, 79 (05) :1295-1303

[2]

[Anonymous], 2003, NCCLS Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically

[3] Coordination to gallium(III) strongly enhances the potency of 2-pyridineformamide thiosemicarbazones against Cryptococcus opportunistic fungi [J].

Bastos, Thaissa de Oliveira ;

Soares, Betania Maria ;

Cisalpino, Patricia Silva ;

Mendes, Isolda Castro ;

dos Santos, Raquel Gouvea ;

Beraldo, Heloisa .

MICROBIOLOGICAL RESEARCH, 2010, 165 (07) :573-577

[4] The wide pharmacological versatility of semicarbazones, thiosemicarbazones and their metal complexes [J].

Beraldo, H ;

Gambino, D .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2004, 4 (01) :31-39

[5]

Bernstein LR, 1998, PHARMACOL REV, V50, P665

[6] Analgesic and Anti-Inflammatory Activities of Salicylaldehyde 2-Chlorobenzoyl Hydrazone (H2LASSBio-466), Salicylaldehyde 4-Chlorobenzoyl Hydrazone (H2LASSBio-1064) and Their Zinc(II) Complexes [J].

Bispo Junior, Walfrido ;

Alexandre-Moreira, Magna S. ;

Alves, Marina A. ;

Perez-Rebolledo, Anayive ;

Parrilha, Gabrieli L. ;

Castellano, Eduardo E. ;

Piro, Oscar E. ;

Barreiro, Eliezer J. ;

Lima, Lidia Moreira ;

Beraldo, Heloisa .

MOLECULES, 2011, 16 (08) :6902-6915

[7] Compositional and structural variety of diphenyllead(IV) complexes obtained by reaction of diphenyllead dichloride with thiosernicarbazones [J].

Casas, JS ;

Castellano, EE ;

Ellena, J ;

Tasende, MSG ;

Sánchez, A ;

Sordo, J ;

Vidarte, MJ .

INORGANIC CHEMISTRY, 2003, 42 (08) :2584-2595

[8] Increasing the antibacterial activity of gallium(III) against Pseudomonas aeruginosa upon coordination to pyridine-derived thiosemicarbazones [J].

da Silva, Jeferson G. ;

Azzolini, Lucas S. ;

Wardell, Solange M. S. V. ;

Wardell, James L. ;

Beraldo, Heloisa .

POLYHEDRON, 2009, 28 (11) :2301-2305

[9] Zinc(II) complexes of 2-pyridine-derived N(4)-p-tolyl thiosemicarbazones: study of in vitro antibacterial activity [J].

Da Silva, Jeferson G. ;

Wardell, Solange M. S. V. ;

Wardell, James L. ;

Beraldo, Heloisa .

JOURNAL OF COORDINATION CHEMISTRY, 2009, 62 (09) :1400-1406

[10] Transition metal complexes of 3-acetylpyridine 4N-(2-pyridyl)thiosemicarbazone (HAPS); structural, spectroscopic, and biological studies [J].

El-Ayaan, Usama .

JOURNAL OF COORDINATION CHEMISTRY, 2012, 65 (04) :629-642

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