Design and synthesis of novel scaffolds for drug discovery: hybrids of beta-D-glucose with 1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-one, the corresponding 1-oxazepine, and 2- and 4-pyridyldiazepines.
[structure: see text]. We describe the syntheses of novel tricyclic scaffolds that incorporate a fusion of a substituted pyranose ring with the seven-membered rings of 1,2,3,4-tetrahydrobenzo[e][1,4]diazepin-5-one and the corresponding oxazepine and pyridyldiazepine to generate the benzodiazepines, and the related heterocycles. In each instance, the pyranose rings contain three protected hydroxyls, suitable for selective derivatization.
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
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Abrous
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Hynes
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Friedrich
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Smith
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Hirschmann
D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D005947:Glucose / Q000737:chemistry*; D015394:Molecular Structure; D010077:Oxazepines / Q000737:chemistry
C429323:1,2,3,4-tetrahydrobenzo(e)(1,4)diazepin-5-one; D010077:Oxazepines; D001569:Benzodiazepines; D005947:Glucose