178035-83-1Relevant articles and documents
Chiral 2-(3′-(5′-p-chlorophenyl)isoxazolidinyl)ethanolamines as conformationally restrained analogs of methyloxyiminomethyl (MOIM) β-adrenergic antagonists: Synthesis, configuration and β-adrenergic properties
Balsamo,Breschi,Chiellini,Cozzini,Domiano,Macchia,Manera,Martinelli,Nencetti,Rossello,Sacca,Scatizzi
, p. 291 - 300 (2007/10/03)
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.
