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Conformations and "nictinic" activites of cyclic analogues of choline aryl ether.

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.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Clark ER,Hughes IE,Smith CF

doi

10.1021/jm00227a022

keywords:

subject

Has Abstract

pub_date

1976-05-01 00:00:00

pages

692-5

issue

5

eissn

0022-2623

issn

1520-4804

journal_volume

19

pub_type

杂志文章

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