ISSN:
0899-0042
Keywords:
5-acetyl-2-methyl-4-methylsulfinyl-6-phenyl-3(2H)-pyridazinone
;
chromatographic chiral resolution
;
absolute configuration
;
X-ray crystallographic analysis
;
antiplatelet activity
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
In a series of 5-acyl-6-phenyl-2,4-substituted-3(2H)-pyridazinones the derivative 1a, with a sulfur stereogenic center, had the most potent activity as human platelet aggregation inhibitor. The resolution of rac-1a was successfully performed by chiral chromatography on Chiralcel OD-R, OD-H, and Chiralpak AD columns and scaled up to a preparative level. The absolute configuration of (-)-(S)-1a was determined by X-ray crystallographic analysis. In vitro human platelet aggregation inhibitory activity was evaluated. Both the enantiomers showed IC50 values in the same micromolar range, but the (-)-(S) isomer was slightly more potent [(S)/(R) potency ratio was 4/1]. Chirality 9:681-685, 1997. © 1997 Wiley-Liss, Inc.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
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