SYNTHESIS AND PHARMACOLOGICAL INVESTIGATION OF THE ENANTIOMERS OF MUSCARONE AND ALLOMUSCARONE
Articolo
Data di Pubblicazione:
1992
Citazione:
SYNTHESIS AND PHARMACOLOGICAL INVESTIGATION OF THE ENANTIOMERS OF
MUSCARONE AND ALLOMUSCARONE / M. De Amici, C. Dallanoce, C. De Micheli, E. Grana, G. Dondi, H. Ladinsky, G.B. Schiavi, F. Zonta. - In: JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0022-2623. - 35:10(1992), pp. 1915-1920.
Abstract:
A strategy based on the use of (R)- and (S)-lactic ester as starting
materials allowed the synthesis of the two enantiomers of muscarone
{[(-)-1 and (+)-1] and allomuscarone [(-5)-5 and (+)-5] in > 98\%
enantiomeric excess. The compounds were examined for their ability to
bind to membranes from cerebral cortex (M1), heart (M2), and salivary
glands (M3) and to recognize affinity agonist states of the muscarinic
receptors. The two pairs of enantiomers were also tested in five
functional assays, and their muscarinic potency was determined. In both
binding and functional tests, (-)-1 (2S,5S) and (-)-5 (2R,5S) were the
eutomers of muscarone and allomuscarone, respectively. The eudismic
ratio of muscarone, evaluated in the functional tests, spanned a range
of 280-440. These values are substantially different from ones
(2,4-10.1) reported in the literatre. From a stereochemical point of
view, muscarone behaves as muscarine and all other major muscarinic
agonists; as a consequence, the hypotheses advanced to account for the
anomalies of muscarone no longer have reason to exist.}
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
M. De Amici, C. Dallanoce, C. De Micheli, E. Grana, G. Dondi, H. Ladinsky, G.B. Schiavi, F. Zonta
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