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|Titolo:||Resolution and muscarinic activity of (+)- and ( – )-4a-methyl-3b- hydroxy-1a -(N,N-dimethylaminomethyl) cyclopentane methiodide [(+)-deoxamuscarine]|
|Autori interni:||TAYEBATI, Seyed Khosrow|
|Data di pubblicazione:||1992|
|Rivista:||PHARMACEUTICAL AND PHARMACOLOGICAL LETTERS|
|Abstract:||The synthesis and resolution of (+)-4- methyl-3-hydroxy-1 -(N pl-dimethylaminomethyl)cyclopentane methiodide [(+)-deoxamuscarine] was achieved by the classical method of fractional crystallization of the diastereomeric salts of the intermediates. The absolute configuration was established by the course of the hydroboration reaction (transformation of 4 to 5) starting from structurally known precursors, and the optical purity by 1H NMR spectra in the presence of (+)-MTPA. The pharmacological data at peripheral muscarinic receptors showed that the most potent enantiomer [(-)-1] had an identical absolute configuration with that of the most potent enantiomer of (+)-muscarine, and the eudismic ratios seemed to reveal a possible heterogeneity between guinea pig ileum and bladder receptors. Considering that enantiomers of muscarinic receptor agonists and antagonists display pharmacological enantioselectivity, which may provide useful information on the site and mode of interaction, we thought it of interest to study the enantioselectivity of the enantiomers of 1. This may have relevance if one considers that enantiomers might display different selectivity for muscarinic receptor subtypes. In fact, little if nothing is known about the structural requirements which determine selectivity to one muscarinic receptor subtype, rather than to another. Furthermore, investigation of enantiomers of active compounds may be useful for achieving better insight into the nature of the active binding site, owing to the finding that enantiomers may exhibit opposite pharmacological effects (agonism vs antagonism).|
|Appare nelle tipologie:||Articolo|
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