Data di Pubblicazione:
1993
Citazione:
SYNTHESIS AND MUSCARINIC ACTIVITY OF THE CHIRAL FORMS OF
METHYLENEMUSCARONES / M. De Amici, C. De Micheli, T. Gianferrara, E. Grana, G. Dondi, H. Ladinsky, G.B. Schiavi. - In: IL FARMACO. - ISSN 0014-827X. - 48:10(1993), pp. 1349-1357.
Abstract:
The synthesis of the two pairs of enantiomers of methylenemuscarones 3
and 4 has been accomplished by using (R)- and (S)-lactic esters as
starting materials. Due to the existence of different muscarinic
receptor subtypes, the compounds were examined for their ability to bind
membranes from cerebral cortex (M1), heart (M2), and salivary glands
(M3) and were assayed in `'in vitro'' functional tests as well. The
results of such an investigation put in evidence that, in both binding
and functional tests, (-)-3 (2S,5S) and (-)-4 (2R,5S) were the eutomers
and shared the stereochemistry of the eutomer of muscarone and
allomuscarone respectively. It is worth noting that the distomer of 3
and 4 behaves as a partial agonist in the cardiac tissue and as a full
agonist in the other preparations. This peculiarity of the chiral forms
of 3 and 4 could account for the remarkable selectivity for the ileum
observed in the corresponding racemates.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
M. De Amici, C. De Micheli, T. Gianferrara, E. Grana, G. Dondi, H. Ladinsky, G.B. Schiavi
Link alla scheda completa: