Absolute configuration of (+)-5-(3-hydroxyphenyl)-5-phenylhydantoin, the major metabolite of 5,5-diphenylhydantoin in the dog

Absolute configuration of (+)-5-(3-hydroxyphenyl)-5-phenylhydantoin, the major metabolite of 5,5-diphenylhydantoin in the dog

5-(3-Hydroxyphenyl)-5-phenylhydantoin (m-HPPH) has been resolved by crystallization of the brucine salts. The (+) enantiomer has been converted to (-)-5-cyclohexyl-5-phenylhydantoin, a compound previously demonstrated to have the R configuration. The R configuration can accordingly be assigned to (+...

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Veröffentlicht in:Journal of medicinal chemistry 1978-12, Vol.21 (12), p.1294-1297
Hauptverfasser: Maguire, James H, Butler, Thomas C, Dudley, Kenneth H
Format: Artikel
Sprache:eng
Schlagworte:
Crystallization
Hydroxylation
Methods
Molecular Conformation
Phenytoin - analogs & derivatives
Phenytoin - chemical synthesis
Phenytoin - metabolism
Stereoisomerism
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Zusammenfassung:5-(3-Hydroxyphenyl)-5-phenylhydantoin (m-HPPH) has been resolved by crystallization of the brucine salts. The (+) enantiomer has been converted to (-)-5-cyclohexyl-5-phenylhydantoin, a compound previously demonstrated to have the R configuration. The R configuration can accordingly be assigned to (+)-m-HPPH, the principal metabolite of 5,5-diphenylhydantoin (phenytoin) in the dog.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00210a023