Resolution, absolute configuration, and cholinergic enantioselectivity of (-)- and (+)-c-2-methyl-r-5-[(dimethylamino)methyl]-1,3-oxathiolane t-3-oxide methiodide and related sulfones.
J Med Chem
; 30(10): 1934-8, 1987 Oct.
Article
en En
| MEDLINE
| ID: mdl-3656366
ABSTRACT
As a continuation of previous studies on chiral cholinergic agonists carrying a 1,3-oxathiolane nucleus, the enantiomers of c-2-methyl-r-5-[(dimethylamino)methyl]-1,3-oxathiolane t-3-oxide methiodide ((+)- and (-)-1) and of cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolane 3,3-dioxide ((+)- and (-)-2) were obtained and their absolute configurations established by synthesis. The cholinergic potency of the four isomers was evaluated in vitro on guinea pig ileum and frog rectus abdominis models, and the results show that (-)-1, which has the same absolute configuration as L-(+)-muscarine, is a selective and potent muscarinic agent. The (+)-1 enantiomer is some hundred times less potent than (-)-1 on the muscarinic guinea pig ileum while, on the same tissue, the corresponding sulfone derivatives ((+)- and (-)-2) show no enantioselectivity.
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Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Sulfonas
/
Tiofenos
/
Receptores Colinérgicos
/
Dimetilaminas
/
Compuestos Heterocíclicos
Límite:
Animals
Idioma:
En
Revista:
J Med Chem
Asunto de la revista:
QUIMICA
Año:
1987
Tipo del documento:
Article
País de afiliación:
Italia