| Summary: | The six new copper(II) coordination compounds [Cu(HL<sup>1</sup>)Cl<sub>2</sub>] (<b>1</b>), [Cu(HL<sup>1</sup>)Br<sub>2</sub>] (<b>2</b>), [Cu(H<sub>2</sub>O)(L<sup>1</sup>)(CH<sub>3</sub>COO)]·1.75H<sub>2</sub>O (<b>3</b>), [Cu(HL<sup>2</sup>)Cl<sub>2</sub>] (<b>4</b>), [Cu(HL<sup>2</sup>)Br<sub>2</sub>] (<b>5</b>), [Cu(H<sub>2</sub>O)(L<sup>2</sup>)(CH<sub>3</sub>COO)] (<b>6</b>) were synthesized with 2-formyl- and 2-acetylpyridine <i>N</i><sup>4</sup>,<i>S</i>-diallylisothiosemicarbazones (HL<sup>1</sup> and HL<sup>2</sup>). The new isothiosemicarbazones were characterized by NMR, FTIR spectroscopy, and X-ray crystallography ([H<sub>2</sub>L<sup>2</sup>]I). All copper(II) coordination compounds were characterized by elemental analysis, FTIR spectroscopy, and molar conductivity of their 1mM methanol solutions. Furthermore, the crystal structure of complex <b>3</b> was determined using single-crystal X-ray diffraction analysis. The studied complexes manifest antibacterial and antifungal activities, that in many cases are close to the activity of medical drugs used in this area, and in some cases even exceed them. The complexes <b>4</b> and <b>5</b> showed the highest indexes of selectivity (280 and 154) and high antiproliferative activity against BxPC-3 cell lines that surpass the activity of Doxorubicin. The complexes <b>1</b>–<b>3</b> also manifest antioxidant activities against cation radicals ABTS<sup>•+</sup> that are close to that of trolox, the antioxidant agent used in medicine.
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