ISSN:
0899-0042
Keywords:
neuroleptic
;
dopamine
;
receptor
;
enantioselectivity
;
schizophrenia
;
stereochemistry
;
isomers
;
racemate
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The relative configuration of the enantiomers of thioridazine was defined to explore the stereochemistry associated with the selective binding of (-)-thioridazine to dopamine D-1 receptors and (+)-thioridazine to D-2 receptors. Using a seven-step stereoconservative synthesis, (-)-(S)-2-piperidinecarboxylic acid was converted to (-)-(S*)-2-(2-chloroethyl)-1-methylpiperidine, a literature (-)-thioridazine synthetic precursor. Accordingly, (-)- and (+)-thioridazine are the (S)- and (R)-enantiomers, respectively.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chir.530030312
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