| Summary: | In an attempt to increase the biological activity of the 1,2,4-triazolo[1,5-<i>a</i>]pyrimidine scaffold through complexation with essential metal ions, the complexes <i>trans</i>-[Cu(mptp)<sub>2</sub>Cl<sub>2</sub>] (<b>1</b>), [Zn(mptp)Cl<sub>2</sub>(DMSO)] (<b>2</b>) (mptp: 5-methyl-7-phenyl-1,2,4-triazolo[1,5-<i>a</i>]pyrimidine), [Cu<sub>2</sub>(dmtp)<sub>4</sub>Cl<sub>4</sub>]·2H<sub>2</sub>O (<b>3</b>) and [Zn(dmtp)<sub>2</sub>Cl<sub>2</sub>] (<b>4</b>) (dmtp: 5,7-dimethyl-1,2,4-triazolo[1,5-<i>a</i>]pyrimidine), were synthesized and characterized as new antiproliferative and antimicrobial species. Both complexes (<b>1</b>) and (<b>2</b>) crystallize in the <i>P</i>2<sub>1</sub>/n monoclinic space group, with the tetrahedral surroundings generating a square-planar stereochemistry in the Cu(II) complex and a tetrahedral stereochemistry in the Zn(II) species. The mononuclear units are interconnected in a supramolecular network through π–π interactions between the pyrimidine moiety and the phenyl ring in (<b>1</b>) while supramolecular chains resulting from C-H∙∙∙π interactions were observed in (<b>2</b>). All complexes exhibit an antiproliferative effect against B16 tumor cells and improved antibacterial and antifungal activities compared to the free ligands. Complex (<b>3</b>) displays the best antimicrobial activity against all four tested strains, both in the planktonic and biofilm-embedded states, which can be correlated to its stronger DNA-binding and nuclease-activity traits.
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