Chiral synthesis and pharmacological evaluation of the enantiomers of SM32, a new analgesic and cognition-enhancing agent.
The enantiomers of 3-alpha-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.
Romanelli
M N
MN
Dipartimento di Scienze Farmaceutiche Università di Firenze, Italy.
Bartolini
A
A
Bertucci
C
C
Dei
S
S
Ghelardini
C
C
Giovannini
M G
MG
Gualtieri
F
F
Pepeu
G
G
Scapecchi
S
S
Teodori
E
E
D000109:Acetylcholine / Q000378:metabolism; D000700:Analgesics / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D001285:Atropine / Q000737:chemistry; D001362:Avoidance Learning / Q000187:drug effects; D001522:Behavior, Animal / Q000187:drug effects; D003071:Cognition / Q000187:drug effects*; D008297:Male; D051379:Mice; D051381:Rats; D017208:Rats, Wistar; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C106486:3-alpha-tropyl-2-(phenylthio)butyrate; D000700:Analgesics; D014326:Tropanes; D001285:Atropine; D000109:Acetylcholine