Data di Pubblicazione:
1995
Citazione:
SYNTHESIS AND PHARMACOLOGICAL INVESTIGATION OF NEW CHIRAL MUSCARINIC
ANTAGONISTS / M. Carnielli, M. De Amici, C. De Micheli, T. Gianferrara, V. Maurich, M. Zacchigna, E. Grana, C. Boselli. - In: IL FARMACO. - ISSN 0014-827X. - 50:1(1995), pp. 21-27.
Abstract:
The two pairs of enantiomers of isoxazolidin-3-ones 3 and 4 were
synthesized by means of Lipase PS-catalyzed hydrolyses of suitable
racemic butyrates. The same butyrates were also employed as key
intermediates in the preparation of racemic 3 and 4. The antimuscarinic
potency of the new compounds was assayed in two in vitro functional
tests. The eutomers (-)-3 and (-)-4 share the same stereochemistry (5R)
of the most potent enantiomer of `'azamuscarone'' 2, a structurally
related muscarinic agonist. Such a spatial arrangement around the chiral
center of 2-4, coupled with the low values of eudismic ratio, represents
an anomaly among the chiral muscarinic ligands. This anomaly was
accounted for by the absence of a chiral center at C-2, a positon whose
configuration is crucial in determining the high enantioselectivity of
muscarinic agonists and antagonists.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
M. Carnielli, M. De Amici, C. De Micheli, T. Gianferrara, V. Maurich, M. Zacchigna, E. Grana, C. Boselli
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