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Synthesis of copper(II) and zinc(II) complexes with chalcone–thiosemicarbazone hybrid ligands: X-ray crystallography, spectroscopy and yeast activity

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Abstract

Four chalcone–thiosemicarbazones (C-TSCs) of the type 2-((E)-3-(4-R-phenyl)-1-phenylallylidene)-N-phenylhydrazinecarbothioamide, where R = Cl (HL1), NO2 (HL2), CH3 (HL3) or CN (HL4), were prepared in good yields from the reaction of the respective chalcone with 4-phenyl-3-thiosemicarbazide and HCl in EtOH. Reaction of HL with CuCl2·2H2O or ZnCl2 in the presence of Et3N afforded the complexes [M(L)2], M = Cu(II) or Zn(II). X-ray diffraction analysis revealed that the ligands coordinate in their deprotonated form, in a bidentate fashion through the iminic nitrogen and sulfur atoms. Yeast activities of the compounds were tested, where the ligand HL4 was the most damaging derivative, exhibiting cell viability at about 50%. On the other hand, lipid peroxidation assays revealed that the ligand HL1 was able to better induce membrane damage compared to the other compounds. It has been found that coordination with Cu(II) and Zn(II) did not increase the biological activities of the C-TSCs.

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Acknowledgements

The authors thank the Brazilian agencies CAPES, CNPQ and FAPERJ (Grant: Sediadas E-26/010.002894/2014) for financial support, LDRX-UFF (www.ldrx.uff.br/) for the X-ray diffraction analysis and PPGQ-UFRRJ (http://cursos.ufrrj.br/posgraduacao/ppgq/) for the facilities.

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  1. Guilherme Pereira Guedes

    Present address: Instituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, Centro, Niterói, RJ, CEP 24020-150, Brazil

Authors and Affiliations

  1. Instituto de Química, Universidade Federal Rural do Rio de Janeiro, BR-465, Km 7, Seropédica, RJ, CEP 23890-000, Brazil

    Igor Resendes Barbosa, Isabela da Silva Pinheiro, Alan Douglas Lopes dos Santos, Aurea Echevarria, Carla Marins Goulart, Guilherme Pereira Guedes, Nathally Alves da Costa, Beatriz Martinez de Oliveira e Silva, Cristiano Jorge Riger & Amanda Porto Neves

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Barbosa, I.R., Pinheiro, I.d.S., dos Santos, A.D.L. et al. Synthesis of copper(II) and zinc(II) complexes with chalcone–thiosemicarbazone hybrid ligands: X-ray crystallography, spectroscopy and yeast activity. Transit Met Chem 43, 739–751 (2018). https://doi.org/10.1007/s11243-018-0262-0

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