European Journal of Medicinal Chemistry p. 291 - 300 (1996)
Update date:2022-08-02
Topics:
Balsamo
Breschi
Chiellini
Cozzini
Domiano
Macchia
Manera
Martinelli
Nencetti
Rossello
Sacca
Scatizzi
The chiral N-isopropyl- and N-t-butyl-substituted 2-(3′-(5′-p-chlorophenyl)isoxazolidinyl)ethanolamines 2, 3, which can be viewed as conformationally restrained analogs of the corresponding methyloxyiminomethyl (MOIM) β-adrenergic antagonists 1, were synthesized from optically active precursors with a known absolute configuration. The structure and configuration of the intermediate and final products 2, 3 were assigned on the basis of a comparison of the 1H-NMR spectral data of all compounds, crystallographic analysis of one of the intermediates [(2R,5′S)-7] and knowledge of the configuration of the chiral starting compounds 4. The new isoxazoline derivatives 2, 3 were tested for their affinity towards β1- and β2-adrenoceptors by radioligand binding experiments; compounds showing affinity indices lower than 10 μM on β1-adrenoceptors were also assayed for their β-adrenergic activity by functional tests on isolated preparations. The results showed that the cyclic derivatives 2, 3 possess a capacity to interact with β-receptors which is clearly lower than that of the corresponding MOIM analogs 1.
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