Chiral synthesis and pharmacological evaluation of the enantiomers of SM32, a new analgesic and cognition-enhancing agent

The enantiomers of 3‐α‐tropyl 2‐(phenylthio)butyrate (SM32, 1) were prepared by chiral synthesis and tested for analgesic, cognition‐enhancing, and ACh‐releasing properties. They show enantioselectivity in some of the tests, the eutomer being related in configuration to R‐(+)‐hyoscyamine. Chirality...

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Veröffentlicht in:	Chirality (New York, N.Y.) N.Y.), 1996, Vol.8 (8), p.579-584
Hauptverfasser:	Romanelli, Maria Novella, Bartolini, Alessandro, Bertucci, Carlo, Dei, Silvia, Ghelardini, Carla, Giovannini, Maria Grazia, Gualtieri, Fulvio, Pepeu, Giancarlo, Scapecchi, Serena, Teodori, Elisabetta
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetylcholine - metabolism ACh releaser analgesic Analgesics - chemical synthesis Analgesics - chemistry Analgesics - pharmacology Animals Atropine - chemistry Avoidance Learning - drug effects Behavior, Animal - drug effects Cognition - drug effects cognition-enhancer enantioselectivity Male Mice Rats Rats, Wistar Stereoisomerism Tropanes - chemical synthesis Tropanes - chemistry Tropanes - pharmacology α-tropyl esters
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Zusammenfassung:	The enantiomers of 3‐α‐tropyl 2‐(phenylthio)butyrate (SM32, 1) were prepared by chiral synthesis and tested for analgesic, cognition‐enhancing, and ACh‐releasing properties. They show enantioselectivity in some of the tests, the eutomer being related in configuration to R‐(+)‐hyoscyamine. Chirality 8:579–584, 1996. © 1997 Wiley‐Liss, Inc.
ISSN:	0899-0042 1520-636X
DOI:	10.1002/(SICI)1520-636X(1996)8:8<579::AID-CHIR7>3.0.CO;2-4