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.
Abrous
L
L
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Hynes
J
J
Friedrich
S R
SR
Smith
A B
AB
Hirschmann
R
R
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