European Journal of Medicinal Chemistry p. 751 - 764 (1992)
Update date:2022-08-05
Topics:
Balsamo A
Breschi, MC
Chini, M
Domiano, M
Giannaccini, G
et al.
The diastereoisomeric N-isopropyl- and N-t-butyl-substituted 2-(5'-(3'-phenyl)- and 2-(5'-(3'-isopropyl)isoxazolidinyl)ethanolamines (5-8), which can be viewed as conformationally restrained analogs of the corresponding β-blocking oxime ethers 10 and 11, were synthesized.The relative configurations of (5-8) were assigned by 1H-NMR studies and by the determination of the solid state structure of one of the new compounds (6a).The new isoxazoline derivatives (5-8) were tested both by radioligand binding assays and by functional tests on isolated preparations.Compounds5a-8a were found to retain, albeit to a lower extent, the β-blocking properties of the corresponding oxime ethers 10a and 11a, thus indicating that these last compounds may prove to be still capable of interacting with the β-receptors, even if their C = NOCH2 portion is constrained in a conformationally semi-rigid isoxazoline structure.Possible rationalizations of the results were sought by comparing the conformations and the molecular reactivity of model compounds of the isoxazolines 5-8 and of the oxime ethers 10 and 11. adrenergic drugs / β-blocking agents / 2-(5'-isoxazolidinyl)-ethanolamines
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