Biaryls and heterobiaryls as α-glucosidase and protein tyrosine phosphatase inhibitors

Various 6-aryl-4-substituted-2H-pyran-2-one-3-carbonitriles (1a–d) have been synthesized as precursor for the synthesis of 3,4-dihydro-1H-isothiochroman (2a) and benzocycloalkanes (2b–e). Highly functionalized 9-thiaphenanthrene (3b) and phenanthrene (3a) have also been obtained from the reaction of 1c with thiochroman-4-one and 1-tetralone separately. Similarly 4 has been obtained by the ring transformation of 1d by 4-trifluoromethylacetophenone. Most of the synthesized compounds were evaluated for α-glucosidase and protein tyrosine phosphatase inhibitory activities. Some of the compounds, 2a, 3a and b and 4 displayed better α-glucosidase inhibitory activity compared to standard drug acarbose.