Further structure-activity relations of heterocyclic analogues of hemicholinium-3
- 1 January 1970
- journal article
- Published by Oxford University Press (OUP) in Journal of Pharmacy and Pharmacology
- Vol. 22 (1) , 20-25
- https://doi.org/10.1111/j.2042-7158.1970.tb08379.x
Abstract
The importance of the 3-methyl group on the pyridinium ring of bis-quaternary nitrogen salts for hemicholinium-3-like activity having been conditionally established (Benz & Long, 1969a, b), derivatives containing classical isosteres of the 3-methyl group and the three oxidation states of the 3-methyl group were examined. Oxidation of the 3-methyl group to -CH2OH decreased activity tenfold. Subsequent oxidation to -CHO and -COOH further decreased activity. When the 3-methyl group was replaced by a halogen, activity was maintained by the iodo-derivative but decreased as the size of the halogen decreased and as the electronegativity increased. Substitution of an ethyl group for the 3-methyl decreased activity twofold, whereas replacement with -OH eliminated activity.Keywords
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