| Summary: | For the first time, a thiosemicarbazone-type ligand containing a paracetamol structural unit was synthesized. Five new coordination compounds based on copper(II) salts: [Cu(L)CH<sub>3</sub>COO] (<b>1</b>), [{Cu(L)Cl}<sub>2</sub>]·H<sub>2</sub>O (<b>2</b>), [Cu(L)H<sub>2</sub>O·DMF]NO<sub>3</sub> (<b>3</b>), [Cu(L)Br] (<b>4</b>), [Cu(L)H<sub>2</sub>O]ClO<sub>4</sub> (<b>5</b>), were obtained, where <b>HL</b> is <i>N</i>-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide. The new <b>HL</b> was characterized by NMR, FTIR, spectroscopy, and X-ray crystallography. All copper(II) coordination compounds were characterized by elemental analysis, FTIR, EPR spectroscopy, and molar electrical conductivity. Furthermore, single crystal X-ray diffraction analysis elucidated the structures of thiosemicarbazone <b>HL</b> as well as complexes <b>1–3</b>. All compounds were tested for antimicrobial, antifungal, and antioxidant activities, and their toxicity to <i>Daphnia magna</i> was studied. Biological evaluation has revealed that most of the synthesized compounds demonstrate promising antibacterial, antifungal, and antioxidant activities. In many cases, their antibacterial/antifungal activity is comparable to that of certain drugs used in medicine for these purposes, and in some cases, even surpasses them. <b>HL</b> and complexes <b>2–5</b> exhibit antioxidant activity that surpasses that of Trolox. Furthermore, <b>HL</b> and complex <b>2</b> display virtually no toxicity to <i>D. magna.</i>
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