The enantiomers of 2-[[[2-(2,6-dimethoxyphenoxy)ethyl]amino]methyl]-1,4-benzoxathian hydrochloride (1: benoxathian) were prepared from the chiral 1,4-benzoxathian-2-carboxylic acids [(+)- and (−)-3] which in turn were obtained through the resolution of the racemic acid with R- and S-alpha-methylbenzylamine. Their blocking activities and relative selectivities on alpha1- and alpha2-adrenoreceptors were evaluated on isolated rat vas deferens. For alpha1-adrenoreceptors the enantiomer (−)-1 was 10 times more potent than the enantiomer (+)-1, whereas no significant difference between the blocking activity of the enantiomers was observed for alpha2-adrenoreceptors. Furthermore, the enantiomer (−)-1 showed high activity and selectivity toward the alpha1-adrenoreceptor (pA2 = 9.36; selectivity ratio = 1230) which may have relevance in the characterization of alpha-adrenoreceptor subtypes.

Resolution of the potent alpha1-adrenoreceptor antagonist 2-[[[2-(2,6-dimethoxyphenoxy)ethyl]amino]methyl]-1,4-benzoxathian (benoxathian)

QUAGLIA, Wilma;
1987-01-01

Abstract

The enantiomers of 2-[[[2-(2,6-dimethoxyphenoxy)ethyl]amino]methyl]-1,4-benzoxathian hydrochloride (1: benoxathian) were prepared from the chiral 1,4-benzoxathian-2-carboxylic acids [(+)- and (−)-3] which in turn were obtained through the resolution of the racemic acid with R- and S-alpha-methylbenzylamine. Their blocking activities and relative selectivities on alpha1- and alpha2-adrenoreceptors were evaluated on isolated rat vas deferens. For alpha1-adrenoreceptors the enantiomer (−)-1 was 10 times more potent than the enantiomer (+)-1, whereas no significant difference between the blocking activity of the enantiomers was observed for alpha2-adrenoreceptors. Furthermore, the enantiomer (−)-1 showed high activity and selectivity toward the alpha1-adrenoreceptor (pA2 = 9.36; selectivity ratio = 1230) which may have relevance in the characterization of alpha-adrenoreceptor subtypes.
1987
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11581/242159
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