Currently, the synthesis of oxygen-containing heterocyclic compounds containing a fused benzene ring system with a pyrone cycle, represented by 4-hydroxycoumarin (4-hydroxy-2H-chromen-2-one), is of great importance due to their broad spectrum of biological activity. We found it interesting to conduct reactions of 1,5-dicarbonyl compounds based on 4-hydroxycoumarin with N-nucleophiles, both from a fundamental point of view and from the perspective of the practical application of the resulting products. The interaction of 4-hydroxy-3-(3- oxo-1-aryl-3-(4-aminophenyl)propyl)-2H-chromen-2-ones with hydrazine hydrate upon heating in isopropyl alcohol led to the formation of products of nucleophilic attack on the carbonyl groups of the acyclic and coumarin fragments of the substrate, yielding 3-(3-(4-aminophenyl)- 1-aryl-3-hydrazinylidenepropyl)-4-hydrazinylidenechroman-2-ones with good yields. In a similar reaction with 5-amino-2-methyl-1,3-thiazole in ethanol, 3-(3-(4-aminophenyl)-1-aryl-3-((2-methylthiazol-5-yl)imino)propyl)-4-hydroxy-2H-chromen-2-ones have been obtained – the result of the reagent attacking the carbonyl group of the acyclic fragment of the substrate. The composition and structure of the obtained compounds have been established based on elemental analysis, IR, and NMR spectroscopy data. We also performed a virtual screening of the biological activity of the obtained compounds in the PASS Online program, which revealed a high probability of all products exhibiting inhibitory activity against β-glucuronidase. This suggests that all the compounds we have obtained may be promising in the prevention of cancerous tumors. Additionally, molecular docking has been performed, showing that the products we have obtained are potentially better inhibitors of β-glucuronidase than the reference drug, scopoletin.