Synthesis of bicyclic biaryls as glucose-6-phosphatase inhibitors Original Research Article

Biaryls, 7-naphthyl-5-s-amino-2,3-dihydrobenzo[b]thiophene-4-carbonitriles (3a–e), 8-(1-naphthyl)-6-s-amino-isothiochroman-5-carbonitriles (6a–d), 4-(1-naphthyl)-2-s-aminobezocycloalkene-1-carbonitriles (6e–j), 8-naphthyl-6-s-amino-2-ethyl-1,2,3,4-tetrahydro-isoquinoline-5-carbonitrle (6k–n), 1-naphthyl-3-s-amino-10H-9-thia-phenantherene-4-carbonitriles (8a–e) and 1-(1-naphthyl)-3-s-amino-9,10-dihydrophenantherene-4-carbonitriles (8f–i) have been prepared through carbanion induced ring transformation reactions of 6-naphthyl-3-cyano-4-s-amino-2H-pyran-2-ones (1) from respective ketones (2, 5, and 7). These compounds have been evaluated for their glucose-6-phosphatase inhibitory activity and only 6a, c, j, m, c, d, h displayed significant inhibition of the glucose-6-phosphatase.