RESUMO
Two trans-alpha,beta-dibenzyl-gamma-butyrolactone lignans carrying a hydroxyl group at the beta-benzylic carbon atom and a alpha-hydroxy alpha,beta-dibenzyl-gamma-butyrolactone lignan were synthesized in racemic form using the tandem conjugate addition reaction to construct the basic lignan skeleton. Subsequent reaction steps involved either a catalytic reduction of the regenerated keto group to the alcohol, or a hydrogenolysis to benzylic methylene followed by lactone enolate formation and oxidation to give the alpha-hydroxybutyrolactones. These procedures were applied for the synthesis of 7'-hydroxyenterolactones and 7'-hydroxymatairesinols, and 8-hydroxyenterolactones, respectively. The diastereomeric mixtures of these compounds were separated either by HPLC techniques or column chromatography and the structures were elucidated using NMR spectroscopy.
Assuntos
Álcoois/química , Lactonas/síntese química , Lignanas/síntese química , Extratos Vegetais/química , Antineoplásicos Fitogênicos/síntese química , Antineoplásicos Fitogênicos/química , Cromatografia , Cromatografia Líquida de Alta Pressão , Humanos , Lactonas/química , Lignanas/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Estereoisomerismo , Árvores/químicaRESUMO
A series of variably substituted derivatives of lignan lactones and diols were prepared using tandem conjugate addition reaction as a key step. These theoretical precursors of the mammalian lignans enterolactone 1 and enterodiol 3 are moderate or weak inhibitors of human aromatase activity.
Assuntos
4-Butirolactona/análogos & derivados , Inibidores da Aromatase , Catecóis/síntese química , Catecóis/farmacologia , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/farmacologia , Fenóis/síntese química , Fenóis/farmacologia , 4-Butirolactona/síntese química , 4-Butirolactona/química , 4-Butirolactona/farmacologia , Humanos , Lignanas/químicaRESUMO
Four homologous retention index standard series, the alkylmethylhydantoins, alkylhydantoins, alkylmaleimides and alkylbis(trifluoromethyl)phosphine sulphides, were evaluated for the screening of blood samples for acidic and neutral drugs on Ultra 2 and HP-1701 capillary columns over a six-month period. An index series consisting of actual drug substances was used as a standard of comparison. All the series produced high precision, and the precision differences between the series were rather small. Considering the limitations of the other series, the alkylmethylhydantoins and alkylhydantoins turned out to be the most feasible internal retention index standard series in the present dual column setting.
