Racemic and optically active 1,3,3-trimethyl-4-phenyl-4-(propionyloxy)piperidine

The preparation and resolution of 1,3,3-trimethyl-4-phenyl-4-(propionyloxy)piperidine (5,3-methylprodine) are described, and the results of the antinociceptive activities of the products by hot-plate (mice) and tail-withdrawal (rats) tests are shown to support proposals made from a recent analysis o...

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Veröffentlicht in:	Journal of medicinal chemistry 1985-12, Vol.28 (12), p.1947-1949
Hauptverfasser:	Ahmed, F. R, Laws, G. F, Madani, A. E, Casy, A. F
Format:	Artikel
Sprache:	eng
Schlagworte:	Alphaprodine - analogs & derivatives Alphaprodine - chemical synthesis Analgesia Animals Chemical Phenomena Chemistry Condensed matter: structure, mechanical and thermal properties Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Mice Molecular Conformation Organic chemistry Organic compounds Physics Preparations and properties Rats Structure of solids and liquids crystallography Structure of specific crystalline solids Structure-Activity Relationship X-Ray Diffraction
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Beschreibung
Zusammenfassung:	The preparation and resolution of 1,3,3-trimethyl-4-phenyl-4-(propionyloxy)piperidine (5,3-methylprodine) are described, and the results of the antinociceptive activities of the products by hot-plate (mice) and tail-withdrawal (rats) tests are shown to support proposals made from a recent analysis of the stereochemical structure-activity relationships of C-methyl derivatives of the reversed ester of meperidine. Data of absolute configuration were obtained by X-ray crystallography of a hydrobromide salt.
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm00150a031