NOVEL ZINC(II) DERIVATIVES OF PHENOL SCHIFF BASES: SYNTHESIS, CHARACTERISATION, CRYSTAL STRUCTURE AND ANTIMICROBIAL ACTIVITY
DOI :
https://doi.org/10.18540/jcecvl4iss1pp0019-0027Mots-clés :
Schiff bases, zinc(II) complexes, crystal structure, antibacterial activityRésumé
Zinc(II)-Schiff base derivatives of general formula [Zn(L)Cl]n.xH2O {n = 2; x = 1, L = 3-hmp (1), L = 4-hmp (2); x = 0, L = hmyp (3)} were synthesized by the condensation reaction of aminophenol with 2-hydroxybenzaldehyde. The Schiff bases in complex-1, 2 and 3 are bonded to the metal through the nitrogen and oxygen atoms. These complexes have dimeric structures with bridging oxygen atoms; the metal is at the centre of a tetrahedron in complex-1 and 2, and at the centre of a square pyramidal geometry in complex-3 according to the X-ray diffraction analyses. They were characterized by IR, NMR (1H, 13C), molar conductivity, melting point and microanalyses. The bioassay of these Zn(II) derivatives on strains of S. aureus, B. subtillis, E. coli and S. typhimurium showed minimum inhibitory concentration (MIC) between 60 and 520 µM which is within the range reported in the literature for Zn(II)-Schiff base compounds. Complex-2 showed the best antibacterial result with MIC of 65 µM on the Gram-positive S. aureus and B. subtillis bacteria.
Compostos de zinc(II) com bases de Schiff de fórmula geral [Zn(L)Cl]n.xH2O {n = 2; x = 1, L = 3-hmp (1), L = 4-hmp (2); x = 0, L = hmyp (3)} foram preparados mediante reação de condensação entre aminofenol com 2-hidroxibenzaldeído. As bases de Schiff nos complexos 1, 2 e 3 formam ligações ao centro metálico via os átomos de nitrogênio e oxigênio. Estes compostos têm uma estrutura dimérica com átomos de oxigênio em ponte. O metal se encontra no centro de um tetraedro (1 e 2) e de uma pirâmide de base quadrada (3), segundo análise por difração de raios-X. Os compostos foram caracterizados por IR, RMN (1H e 13C), condutividade molar, pontos de fusão e microanálise. Ensaios biológicos em cepas de S. aureus, B. subtillis, E. coli e S. typhimurium mostraram MICs entre 60 e 520 µM. O complexo 2 mostrou o melhor resultado bactericida com MIC de 65 µM contra as bactérias Gram-positivas.
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Références
ABDALLAH, S. M. et al. Spectroscopic study of molecular structures of novel Schiff base derived from o-phthaldehyde and 2-aminophenol and its coordination compounds together with their biological activity. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 73, n. 5, p. 833-840, 2009.
ABDEL-RAHMAN, L. H. et al. Design, characterization, teratogenicity testing, antibacterial, antifungal and DNA interaction of few high spin Fe(II) Schiff base amino acid complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 111, p. 266-276, 2013.
ADDISON, A. W. et al. Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2[prime or minute]-yl)-2,6-dithiaheptane]copper(II) perchlorate. Journal of the Chemical Society, Dalton Transactions, n. 7, p. 1349-1356, 1984.
ADLY, O. M. I.; TAHA, A.; FAHMY, S. A. Synthesis, spectral characterization, molecular modeling and antimicrobial activity of new potentially N2O2 Schiff base complexes. Journal of Molecular Structure, v. 1054-1055, n. Supplement C, p. 239-250, 2013.
ALAGHAZ, A.-N. M. A. et al. Synthesis, spectroscopic identification, thermal, potentiometric and antibacterial activity studies of 4-amino-5-mercapto-S-triazole Schiff’s base complexes. Journal of Molecular Structure, v. 1087, p. 60-67, 2015.
ARJMAND, F.; SAYEED, F.; MUDDASSIR, M. Synthesis of new chiral heterocyclic Schiff base modulated Cu(II)/Zn(II) complexes: Their comparative binding studies with CT-DNA, mononucleotides and cleavage activity. Journal of Photochemistry and Photobiology B: Biology, v. 103, n. 2, p. 166-179, 2011.
BAGIHALLI, G. B.; BADAMI, P. S.; PATIL, S. A. Synthesis, spectral characterization and in vitro biological studies of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases. Journal of Enzyme Inhibition and Medicinal Chemistry, v. 24, n. 2, p. 381-394, 2009.
BLESSING, R. H. An empirical correction for absorption anisotropy. Acta Crystallographica, Section A: Foundations of Crystallography, v. 51, p. 33-38, 1995.
CREAVEN, B. S. et al. Anticancer and antifungal activity of copper(II) complexes of quinolin-2(1H)-one-derived Schiff bases. Inorganica Chimica Acta, v. 363, n. 14, p. 4048-4058, 2010.
CRYSALISRED. Oxford Diffraction Ltda: (release 17-11-2008 CrysAlis171.NET) p. 2008.
DHAHAGANI, K. et al. Synthesis and spectral characterization of Schiff base complexes of Cu(II), Co(II), Zn(II) and VO(IV) containing 4-(4-aminophenyl)morpholine derivatives: Antimicrobial evaluation and anticancer studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 117, p. 87-94, 2014.
FARRUGIA, L. J. ORTEP-3 for windows - a version of ORTEP-III with a graphical user interface (GUI). Journal of Applied Crystallography, v. 30, n. 5, p. 565-565, 1997.
GALINI, M. et al. Structural characterization and electrochemical studies of Co(II), Zn(II), Ni(II) and Cu(II) Schiff base complexes derived from 2-((E)-(2-methoxyphenylimino)methyl)-4-bromophenol; Evaluation of antioxidant and antibacterial properties. Inorganica Chimica Acta, v. 461, p. 167-173, 2017.
GEETA, B. et al. Binuclear cobalt(II), nickel(II), copper(II) and palladium(II) complexes of a new Schiff-base as ligand: Synthesis, structural characterization, and antibacterial activity. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 77, n. 4, p. 911-915, 2010.
HU, X. M. et al. Synthesis, crystal structures, and antimicrobial activity of copper(II) and zinc(II) complexes derived from 2-bromo-4-chloro-6-[(2-morpholin-4-ylethylimino)methyl]phenol. Russian Journal of Coordination Chemistry, v. 42, n. 6, p. 418-422, 2016.
KACZMAREK, M. T. et al. Self-assembled synthesis, characterization and antimicrobial activity of zinc(II) salicylaldimine complexes. Inorganica Chimica Acta, v. 362, n. 9, p. 3127-3133, 2009.
KURSUNLU, A. N. et al. Synthesis, spectroscopic characterization and antimicrobial studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with Schiff bases derived from 5-bromo-salicylaldehyde. Journal of Molecular Structure, v. 1048, p. 476-481, 2013.
MACRAE, C. F. et al. Mercury: visualization and analysis of crystal structures. Journal of Applied Crystallography, v. 39, p. 453-457, 2006.
NAKAMOTO, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry. 5th. New York: John Wiley & Sons Inc., 1997.
NCCLS. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. In: (Ed.). NCCLS document M27-A2. Approved Standard - Second Edition. Pennsylvania, USA: Wayne, v.22, 2002.
NCCLS. Reference Method for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. In: (Ed.). NCCLS document M7-A6. Pennsylvania, USA, 2003. ISBN 1-56238-486-4.
PRAKASH, A. et al. Synthesis and characterization of bioactive zinc(II) and cadmium(II) complexes with new Schiff bases derived from 4-nitrobenzaldehyde and acetophenone with ethylenediamine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 76, n. 3, p. 356-362, 2010.
QIAO, X. et al. Study on potential antitumor mechanism of a novel Schiff Base copper(II) complex: Synthesis, crystal structure, DNA binding, cytotoxicity and apoptosis induction activity. Journal of Inorganic Biochemistry, v. 105, n. 5, p. 728-737, 2011.
SAKAGUCHI, S. et al. Chiral Palladium(II) Complexes Possessing a Tridentate N-Heterocyclic Carbene Amidate Alkoxide Ligand: Access to Oxygen-Bridging Dimer Structures. Angewandte Chemie International Edition, v. 47, n. 48, p. 9326-9329, 2008.
SANTOS, A. F. D. S.; OLIVEIRA, L. L. D.; MAIA, J. R. D. S. Synthesis, Characterisation and Antimicrobial Activity of Dimeric and Monomeric Copper(II)-Schiff Base Complexes IOSR Journal of Applied Chemistry (IOSR-JAC), v. 9, n. 12, p. 54-62, 2016.
SHELDRICK, G. M. SHELXL-97 - A Program for Crystal Structure Refinement: University of Goettingen, Germany 1997.
SINGH, B. K. et al. Spectroscopic, electrochemical and biological studies of the metal complexes of the Schiff base derived from pyrrole-2-carbaldehyde and ethylenediamine. Arabian Journal of Chemistry, v. 10, n. 1, p. S472-S483, 2017.
SINGH, B. K. et al. Spectroscopic characterization and biological activity of Zn(II), Cd(II), Sn(II) and Pb(II) complexes with Schiff base derived from pyrrole-2-carboxaldehyde and 2-amino phenol. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 76, n. 3–4, p. 376-383, 2010.
SINGH, H. L.; SINGH, J. Synthesis, spectral, 3D molecular modeling and antibacterial studies of dibutyltin (IV) Schiff base complexes derived from substituted isatin and amino acids. Natural Science, v. 04, n. 03, p. 9, 2012.
TAGHIZADEH, L. et al. New tetrahedral zinc halide Schiff base complexes: Synthesis, crystal structure, theoretical, 3D Hirshfeld surface analyses, antimicrobial and thermal studies. Materials Science and Engineering: C, v. 77, p. 229-244, 2017.
TAVMAN, A.; BOZ, I.; BIRTEKSÖZ, A. S. Spectral characterization and antimicrobial activity of 2-(5-chloro/nitro-1H-benzimidazol-2-yl)-4-bromo/nitro-phenols and their zinc(II) complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 77, n. 1, p. 199-206, 2010.
WEN, H.-R. et al. Syntheses, structures and properties of chiral dinuclear zinc complexes with Schiff-base ligands. Inorganic Chemistry Communications, v. 20, p. 303-306, 2012.
XUE, L. W. et al. Synthesis, structures, and antimicrobial activity of nickel(II) and zinc(II) complexes with Schiff bases derived from 3-bromosalicylaldehyde. Russian Journal of Coordination Chemistry, v. 39, n. 12, p. 872-876, 2013.
XUE, L. W. et al. Synthesis, structures, and antimicrobial activity of nickel(II) and Zinc(II) complexes with 5-methoxy-2-[(3-methylaminopropylimino)methyl]phenol. Russian Journal of Coordination Chemistry, v. 37, n. 4, p. 262, 16 2011.
ZACCHINO, S. A.; GUPTA, M. P. Manual de técnicas in vitro para la deteccíon de compuestos antifúngicos. Corpus Libros Médicos y Científicos, 2007.
ABDEL-RAHMAN, L. H. et al. Design, characterization, teratogenicity testing, antibacterial, antifungal and DNA interaction of few high spin Fe(II) Schiff base amino acid complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 111, p. 266-276, 2013.
ADDISON, A. W. et al. Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2[prime or minute]-yl)-2,6-dithiaheptane]copper(II) perchlorate. Journal of the Chemical Society, Dalton Transactions, n. 7, p. 1349-1356, 1984.
ADLY, O. M. I.; TAHA, A.; FAHMY, S. A. Synthesis, spectral characterization, molecular modeling and antimicrobial activity of new potentially N2O2 Schiff base complexes. Journal of Molecular Structure, v. 1054-1055, n. Supplement C, p. 239-250, 2013.
ALAGHAZ, A.-N. M. A. et al. Synthesis, spectroscopic identification, thermal, potentiometric and antibacterial activity studies of 4-amino-5-mercapto-S-triazole Schiff’s base complexes. Journal of Molecular Structure, v. 1087, p. 60-67, 2015.
ARJMAND, F.; SAYEED, F.; MUDDASSIR, M. Synthesis of new chiral heterocyclic Schiff base modulated Cu(II)/Zn(II) complexes: Their comparative binding studies with CT-DNA, mononucleotides and cleavage activity. Journal of Photochemistry and Photobiology B: Biology, v. 103, n. 2, p. 166-179, 2011.
BAGIHALLI, G. B.; BADAMI, P. S.; PATIL, S. A. Synthesis, spectral characterization and in vitro biological studies of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases. Journal of Enzyme Inhibition and Medicinal Chemistry, v. 24, n. 2, p. 381-394, 2009.
BLESSING, R. H. An empirical correction for absorption anisotropy. Acta Crystallographica, Section A: Foundations of Crystallography, v. 51, p. 33-38, 1995.
CREAVEN, B. S. et al. Anticancer and antifungal activity of copper(II) complexes of quinolin-2(1H)-one-derived Schiff bases. Inorganica Chimica Acta, v. 363, n. 14, p. 4048-4058, 2010.
CRYSALISRED. Oxford Diffraction Ltda: (release 17-11-2008 CrysAlis171.NET) p. 2008.
DHAHAGANI, K. et al. Synthesis and spectral characterization of Schiff base complexes of Cu(II), Co(II), Zn(II) and VO(IV) containing 4-(4-aminophenyl)morpholine derivatives: Antimicrobial evaluation and anticancer studies. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 117, p. 87-94, 2014.
FARRUGIA, L. J. ORTEP-3 for windows - a version of ORTEP-III with a graphical user interface (GUI). Journal of Applied Crystallography, v. 30, n. 5, p. 565-565, 1997.
GALINI, M. et al. Structural characterization and electrochemical studies of Co(II), Zn(II), Ni(II) and Cu(II) Schiff base complexes derived from 2-((E)-(2-methoxyphenylimino)methyl)-4-bromophenol; Evaluation of antioxidant and antibacterial properties. Inorganica Chimica Acta, v. 461, p. 167-173, 2017.
GEETA, B. et al. Binuclear cobalt(II), nickel(II), copper(II) and palladium(II) complexes of a new Schiff-base as ligand: Synthesis, structural characterization, and antibacterial activity. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 77, n. 4, p. 911-915, 2010.
HU, X. M. et al. Synthesis, crystal structures, and antimicrobial activity of copper(II) and zinc(II) complexes derived from 2-bromo-4-chloro-6-[(2-morpholin-4-ylethylimino)methyl]phenol. Russian Journal of Coordination Chemistry, v. 42, n. 6, p. 418-422, 2016.
KACZMAREK, M. T. et al. Self-assembled synthesis, characterization and antimicrobial activity of zinc(II) salicylaldimine complexes. Inorganica Chimica Acta, v. 362, n. 9, p. 3127-3133, 2009.
KURSUNLU, A. N. et al. Synthesis, spectroscopic characterization and antimicrobial studies of Co(II), Ni(II), Cu(II) and Zn(II) complexes with Schiff bases derived from 5-bromo-salicylaldehyde. Journal of Molecular Structure, v. 1048, p. 476-481, 2013.
MACRAE, C. F. et al. Mercury: visualization and analysis of crystal structures. Journal of Applied Crystallography, v. 39, p. 453-457, 2006.
NAKAMOTO, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry. 5th. New York: John Wiley & Sons Inc., 1997.
NCCLS. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. In: (Ed.). NCCLS document M27-A2. Approved Standard - Second Edition. Pennsylvania, USA: Wayne, v.22, 2002.
NCCLS. Reference Method for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. In: (Ed.). NCCLS document M7-A6. Pennsylvania, USA, 2003. ISBN 1-56238-486-4.
PRAKASH, A. et al. Synthesis and characterization of bioactive zinc(II) and cadmium(II) complexes with new Schiff bases derived from 4-nitrobenzaldehyde and acetophenone with ethylenediamine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 76, n. 3, p. 356-362, 2010.
QIAO, X. et al. Study on potential antitumor mechanism of a novel Schiff Base copper(II) complex: Synthesis, crystal structure, DNA binding, cytotoxicity and apoptosis induction activity. Journal of Inorganic Biochemistry, v. 105, n. 5, p. 728-737, 2011.
SAKAGUCHI, S. et al. Chiral Palladium(II) Complexes Possessing a Tridentate N-Heterocyclic Carbene Amidate Alkoxide Ligand: Access to Oxygen-Bridging Dimer Structures. Angewandte Chemie International Edition, v. 47, n. 48, p. 9326-9329, 2008.
SANTOS, A. F. D. S.; OLIVEIRA, L. L. D.; MAIA, J. R. D. S. Synthesis, Characterisation and Antimicrobial Activity of Dimeric and Monomeric Copper(II)-Schiff Base Complexes IOSR Journal of Applied Chemistry (IOSR-JAC), v. 9, n. 12, p. 54-62, 2016.
SHELDRICK, G. M. SHELXL-97 - A Program for Crystal Structure Refinement: University of Goettingen, Germany 1997.
SINGH, B. K. et al. Spectroscopic, electrochemical and biological studies of the metal complexes of the Schiff base derived from pyrrole-2-carbaldehyde and ethylenediamine. Arabian Journal of Chemistry, v. 10, n. 1, p. S472-S483, 2017.
SINGH, B. K. et al. Spectroscopic characterization and biological activity of Zn(II), Cd(II), Sn(II) and Pb(II) complexes with Schiff base derived from pyrrole-2-carboxaldehyde and 2-amino phenol. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 76, n. 3–4, p. 376-383, 2010.
SINGH, H. L.; SINGH, J. Synthesis, spectral, 3D molecular modeling and antibacterial studies of dibutyltin (IV) Schiff base complexes derived from substituted isatin and amino acids. Natural Science, v. 04, n. 03, p. 9, 2012.
TAGHIZADEH, L. et al. New tetrahedral zinc halide Schiff base complexes: Synthesis, crystal structure, theoretical, 3D Hirshfeld surface analyses, antimicrobial and thermal studies. Materials Science and Engineering: C, v. 77, p. 229-244, 2017.
TAVMAN, A.; BOZ, I.; BIRTEKSÖZ, A. S. Spectral characterization and antimicrobial activity of 2-(5-chloro/nitro-1H-benzimidazol-2-yl)-4-bromo/nitro-phenols and their zinc(II) complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, v. 77, n. 1, p. 199-206, 2010.
WEN, H.-R. et al. Syntheses, structures and properties of chiral dinuclear zinc complexes with Schiff-base ligands. Inorganic Chemistry Communications, v. 20, p. 303-306, 2012.
XUE, L. W. et al. Synthesis, structures, and antimicrobial activity of nickel(II) and zinc(II) complexes with Schiff bases derived from 3-bromosalicylaldehyde. Russian Journal of Coordination Chemistry, v. 39, n. 12, p. 872-876, 2013.
XUE, L. W. et al. Synthesis, structures, and antimicrobial activity of nickel(II) and Zinc(II) complexes with 5-methoxy-2-[(3-methylaminopropylimino)methyl]phenol. Russian Journal of Coordination Chemistry, v. 37, n. 4, p. 262, 16 2011.
ZACCHINO, S. A.; GUPTA, M. P. Manual de técnicas in vitro para la deteccíon de compuestos antifúngicos. Corpus Libros Médicos y Científicos, 2007.
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Publiée
2018-01-23
Comment citer
Maia, J. R. da S., Santos, A. F. da S., Souza, M. C. de, & Diniz, R. (2018). NOVEL ZINC(II) DERIVATIVES OF PHENOL SCHIFF BASES: SYNTHESIS, CHARACTERISATION, CRYSTAL STRUCTURE AND ANTIMICROBIAL ACTIVITY. The Journal of Engineering and Exact Sciences, 4(1), 0019–0027. https://doi.org/10.18540/jcecvl4iss1pp0019-0027
Numéro
Rubrique
Inorganic Chemistry
