Search

The chemistry of α-(arylhydrazono)-β-ketoaldehydes has attracted significant attention due to their use as intermediates in organic synthesis and as building blocks for biologically active compounds. This study presents the synthesis of a novel series of 3,3'-(5-methyl-1-phenyl-1H-pyrazole-3,4-diyl)bis(2-arylhydrazono-3-oxo-propanal) (3a-i), created through coupling reactions of sodium 3,3'-(5-methyl-1-phenyl-1H-pyrazole-3,4-diyl)bis(3-oxoprop-1-en-1-olate) (2) with arenediazonium chloride. The subsequent condensation of these compounds 3a-i with hydrazine hydrate produced a new series of bis(arylazo)-terpyrazole derivatives (5a-i). The new compounds were characterized using spectroscopic techniques and basic evaluations. Furthermore, the electronic absorption spectra of the compounds were recorded in various buffer solutions, and their acidity constants (pK) were calculated. The study also examined the correlation between these constants and Hammett substituent constants. Results indicated that the compounds predominantly exist in the bis-hydrazo form (5A). Compounds 5a-i were evaluated for their antibacterial and anticancer properties against the HepG2 cell line in vitro.