A series of 3-acylhydrazono-4-hydroxycoumarins were synthesized via condensation of 3-acetyl-4-hydroxycoumarin with appropriate hydrazides. The structures of the newly-synthesized compounds were characterized by spectral and elememental analysis or HRMS measurements. Their antioxidant properties were evaluated by using scavenging effects on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical as well as inhibition of lipid peroxidation. Moreover, their ability to inhibit in vitro soybean lipoxygenase has been investigated. They were found to be capable of rapid inactivation of alkylperoxy radicals.
The title compound, C16H12N2O4S, was obtained by the condensation of 3-acetyl-4-hydroxycoumarin with thien-2-ylcarbonyl hydrazide. The pyran ring adopts a 2,4-dione tautomeric form. The benzopyran ring system is almost coplanar with the thiophene ring [dihedral angle 0.9 (2)°]. The exocyclic C=C double bond has an E geometry. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains along the a axis.
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