We report the resolution of racemic (+/-)-1 with (R)-(+)-methylbenzyl isocianate and the synthesis of (R)-1 and (S)-1 via Sharpless chiral epoxidation. The enantio- and tissue-selectivity of such enantiomers, as beta- and alpha-adrenoceptor antagonists, were studied. Compound 1, while confirming the potent beta-blocking activity, displayed a modest enantio-selectivity towards beta-1- and beta-2-adrenoceptors. All the compounds displayed no activity as alpha-adrenoceptor blockers.
Enantiomers of 8-(3-tert-Butylamino-2-hydroxypropoxy)-3,4-dihydro-3-oxo-2H-(1,4)benzothiazine: Racemic Resolution, Chiral Synthesis and Biological Activity.
SCHIAFFELLA, Fausto;FRINGUELLI, Renata;CECCHETTI, Violetta;FRAVOLINI, Arnaldo;
1990
Abstract
We report the resolution of racemic (+/-)-1 with (R)-(+)-methylbenzyl isocianate and the synthesis of (R)-1 and (S)-1 via Sharpless chiral epoxidation. The enantio- and tissue-selectivity of such enantiomers, as beta- and alpha-adrenoceptor antagonists, were studied. Compound 1, while confirming the potent beta-blocking activity, displayed a modest enantio-selectivity towards beta-1- and beta-2-adrenoceptors. All the compounds displayed no activity as alpha-adrenoceptor blockers.File in questo prodotto:
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