RESUMO
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.
Assuntos
4-Hidroxicumarinas/síntese química , 4-Hidroxicumarinas/farmacologia , Antioxidantes/síntese química , Antioxidantes/farmacologia , 4-Hidroxicumarinas/química , Antioxidantes/química , Compostos de Bifenilo/metabolismo , Sequestradores de Radicais Livres/química , Peroxidação de Lipídeos/efeitos dos fármacos , Inibidores de Lipoxigenase/síntese química , Inibidores de Lipoxigenase/química , Inibidores de Lipoxigenase/farmacologia , Estrutura Molecular , Picratos/metabolismo , Proteínas de Plantas/antagonistas & inibidores , Glycine max/enzimologia , Relação Estrutura-AtividadeRESUMO
The title compound, C(16)H(12)N(2)O(4)S, was obtained by the condensation of 3-acetyl-4-hy-droxy-coumarin with thien-2-ylcarbonyl hydrazide. The pyran ring adopts a 2,4-dione tautomeric form. The benzopyran ring system is almost coplanar with the thio-phene ring [dihedral angle 0.9â (2)°]. The exocyclic C=C double bond has an E geometry. The mol-ecular conformation is stabilized by an intra-molecular N-Hâ¯O hydrogen bond. In the crystal, inter-molecular N-Hâ¯O hydrogen bonds link the mol-ecules into chains along the a axis.
