Chromene and hydrazone moieties are present in a number of compounds that exhibit anticancer, antioxidant, antibacterial, antiviral, and other biological properties. In this study, twelve phenolic furanochromene-hydrazone hybrid molecules were synthesized and evaluated for their antioxidant activity. The compounds were synthesized in four steps, beginning with the synthesis of the chromene unit from 2,4-dihydroxybenzaldehyde and 3-methyl-2-butenal under basic conditions, followed by the introduction of an ester substituted furan ring. The ester was converted to a hydrazide, which was subsequently reacted with substituted benzaldehydes containing one, two, or three hydroxy groups to produce the furanochromene-hydrazone hybrids in moderate to excellent yield (64-97%). Antioxidant activity of the furanochromene-hydrazone hybrids were determined using the cupric ion, Cu(II), reducing antioxidant capacity (CUPRAC) assay to determine the influence of the number and location of hydroxy groups on the extent of Cu(II) ion reduction. All the dihydroxy and trihydroxy furanochromene-hydrazone derivatives exhibited higher Cu(II) ion reducing ability compared to ascorbic acid and trolox, while the monohydroxy compounds were less effective.

Synthesis and antioxidant evaluation of phenolic furanochromene-hydrazone hybrids

ACS Spring 2022

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