Synthesis, Spectroscopic Characterization, Structural Analysis, and Evaluation of Anti-Tumor, Antimicrobial, and Antibiofilm Activities of Halogenoaminopyrazoles Derivatives.

New haloaminopyrazole derivatives differing in the number of pyrazole nuclei - and -, respectively, were synthesized and characterized by H-NMR, C-NMR, IR, UV-Vis, and elemental analysis. The single-crystal X-ray diffraction method was used to describe compounds and . When tested on normal NCTC fibroblasts in vitro, the newly synthesized derivatives were shown to be non-cytotoxic at a dosage of 25 μg/mL. Two compounds and showed a high degree of biocompatibility. From the two series of compounds tested on HEp-2 human cervical carcinoma cells, compound showed a more pronounced antiproliferative effect. Gram-positive strains of ATCC25923, ATCC29212, Gram-negative strains of ATCC27853, and strains of ATCC25922 were used to test the newly synthesized compounds antibacterial and antibiofilm properties. Among the studied pyrazole compounds, 2 compounds and with fluorine content on the phenyl ring and 4 compounds , , , and with chlorine content on the phenyl ring were noted, which proved to be the most active compared with the two reference drugs, metronidazole and nitrofurantoin. The six compounds showed a broad spectrum of action against all four tested bacterial strains, the most active being compound , with a chlorine atom in the "4" position of the phenyl nucleus and a MIC of 460 μg/mL. Compounds and showed the best antibiofilm activity against the bacterial strain ATCC25923, with an MBIC of 230 μg/mL.