Conformations and "nictinic" activites of cyclic analogues of choline aryl ether.
J Med Chem
; 19(5): 692-5, 1976 May.
Article
em En
| MEDLINE
| ID: mdl-1271410
ABSTRACT
The synthesis of cis and trans isomers of N,N-N-trimethyl-2-phenoxycyclohexylammonium bromide, cis-N,N,-N-trimethyl-2(2',6'-xylyloxy)cyclohexylammonium bromide, and N,N-dimethyl-3-phenoxypiperidinium bromide is described. Their structures and conformations were determined by NMR and uv absorption spectroscopy, the minimum torsional angles about the aryl-oxygen gond geing 20, 20, 80, and 27 degrees, respectively. Since the piperidinium compound stimulates ganglia, it is concluded the either planarity of the aryl--O--C system is not essential for this type of activity or receptor interaction can involve appreciable bond distortion. The absence of ganglion-stimulant activity in the remaining compounds indicates the need for a transoid arrangement of the O--C--C--N+ system.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Colina
/
Estimulantes Ganglionares
Limite:
Animals
Idioma:
En
Ano de publicação:
1976
Tipo de documento:
Article