RESUMO
A novel short-step methodology for the synthesis in good yields of functionalized coumarins has been developed starting from an activated precursor, the N-hydroxysuccinimide ester of O-acetylsalicylic acid. The procedure is based on a tandem C-acylation-cyclization process under mild reaction conditions. The structure of 3-methoxycarbonyl-4-hydroxy coumarin has been established by X-ray diffraction analysis and its geometry was compared with optimized parameters by means of DFT calculations.
Assuntos
Cumarínicos/química , Cumarínicos/síntese química , Cristalografia por Raios X , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Estrutura Molecular , Teoria QuânticaRESUMO
A series of N-substituted-quinolinone-3-aminoamides and their hybrids containing the alpha-lipoic acid functionality were designed and synthesized as potential bifunctional agents combining antioxidant and anti-inflammatory activity. The new compounds were evaluated for their antioxidant activity and for their ability to inhibit in vitro lipoxygenase as well as for their anti-inflammatory activity in vivo. In general, the derivatives were found to be potent antioxidant or anti-inflammatory agents. The results are discussed in terms of structure-activity relationships and an attempt is made to define the structural features required for activity.
Assuntos
Amidas/síntese química , Anti-Inflamatórios não Esteroides/síntese química , Antioxidantes/síntese química , Quinolonas/síntese química , Ácido Tióctico/análogos & derivados , Ácido Tióctico/síntese química , Amidas/farmacologia , Animais , Anti-Inflamatórios não Esteroides/farmacologia , Antioxidantes/farmacologia , Compostos de Bifenilo/química , Carragenina , Dimetil Sulfóxido/química , Edema/induzido quimicamente , Edema/tratamento farmacológico , Feminino , Hidrazinas/química , Radical Hidroxila/química , Inibidores de Lipoxigenase/síntese química , Inibidores de Lipoxigenase/farmacologia , Masculino , Oxirredução , Picratos , Quinolonas/farmacologia , Ratos , Ratos Endogâmicos F344 , Relação Estrutura-Atividade , Ácido Tióctico/farmacologiaRESUMO
Tetronic acids, 4-hydroxy-5H-furan-2-ones, constitute a class of heterocyclic compounds with potent biological and pharmacological activity. The beta, beta'-tricarbonyl moiety plays an integral role in biological systems and forms a variety of metal complexes. In this report, we present the complexation reactions of 3-ethoxycarbonyl tetronic acids with acetates and chlorides of Cu(II) and Co(II). These complexes have been studied by means of EPR spectroscopy and magnetic susceptibility measurements. From the obtained results, a preliminary complexation mode of the ligand is proposed.