Our chemical and pharmacological experimental programme8'9 in the field of substituted piperidines led to the discovery that 4-(4-hydroxy-4-phenylpiperidino)butyrophenone (I: L = R = H) was a powerful CNS depressant in various species. This unexpected result led us to investigate the CNS depressant properties of a new series of over 500 related basic ketones. The relevant chemical and pharmacological results obtained with these compounds will be presented and discussed in this series of papers.The purpose of this paper is to describe a convenient method of synthesis and some physicochemical properties, as well as some relevant CNS depressant properties in mice of a selected group of
A further step in our studies on compounds derived from norpethidine-type esters, was the investigation of compounds of general structure (I). O ^C-alk-NZ R = (I) COOR'
ZAAs in Part II, R is any substituent, and R' an unsubstituted alkyl or aralkyl-group; 'alk' stands for any branched or unbranched carbon chain other than -CH2CH2-.
SynthesisThe methods of preparing 39 compounds of this series are summarized by the following reaction schemes; the intermediate ketones are described in the literature and the preparation of the norpethidine-type esters has been recorded in Part II.2 I. Condensation of the appropriate haloalkaryl-ketone with the norpethidine-like ester.All but three compounds were synthesized by this method, as follows:1. Two moles of the appropriate secondary amine were heated 271
Since the discovery of pethidine (I) a large number of compounds of related structure have been prepared and screened for analgesic activity. A number of excellent reviews on this subject are available.1-10The purpose of this series of papers is to summarize our experiments with ' compounds related to pethidine ', which are symbolized by general structure II. Structure II represents a secondary or tertiary heterocyclic amine
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