Enantiomers of 8-(3-tert-butylamino-2-hydroxypropoxy)-3,4-dihydro-3-oxo-2H- (1,4)benzothiazine: racemic resolution, chiral synthesis and biological activity |
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| Authors: | F Schiaffella R Fringuelli V Cecchetti A Fravolini P Angeli G Marucci |
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| Affiliation: | Istituto di Chimica Farmaceutica e Technica Farmaceutica, Università di Perugia, Italy. |
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| 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. |
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