Synthesis and Receptor Binding Evaluation of Clavizepine Analogues with No Ring D Substituents

Assembly of the azepine ring of xantheno[9,1-cd]azepines by electrophilic cyclization of sulfonamide acetals provides access to clavizepine analogues in the form of 2,12b-dihydro- or 4-hydroxy-2,3,4,12b-tetrahydro-1H-xantheno[9,1-cd]azepines, in the latter case producing the trans derivative stereos...

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Veröffentlicht in:	Journal of organic chemistry 2006-05, Vol.71 (10), p.3963-3966
Hauptverfasser:	de la Fuente, M. Carmen, Pullan, Shirley E, Biesmans, Ilse, Domínguez, Domingo
Format:	Artikel
Sprache:	eng
Schlagworte:	Azepines - chemistry Chemistry Exact sciences and technology Fumariaceae - chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Models, Molecular Molecular Structure Organic chemistry Preparations and properties Protein Binding Receptors, Serotonin - chemistry Xanthenes - chemistry
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Beschreibung
Zusammenfassung:	Assembly of the azepine ring of xantheno[9,1-cd]azepines by electrophilic cyclization of sulfonamide acetals provides access to clavizepine analogues in the form of 2,12b-dihydro- or 4-hydroxy-2,3,4,12b-tetrahydro-1H-xantheno[9,1-cd]azepines, in the latter case producing the trans derivative stereoselectively. Binding assays for clavizepine and analogues at adrenergic, dopaminergic, and serotonergic receptors are reported.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo052320c