title: Biaryls and heterobiaryls as alpha-glucosidase and protein tyrosine phosphatase inhibitors.
abstract: 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 alpha-glucosidase and protein tyrosine phosphatase inhibitory activities. Some of the compounds, 2a, 3a and b and 4 displayed better alpha-glucosidase inhibitory activity compared to standard drug acarbose.
authors.affiliation: Division of Molecular and Structural Biology, Central Drug Research Institute, Lucknow 226001, India.
authors.forename: Ashoke
authors.initials: A
authors.lastname: Sharon
authors.forename: Ramendra
authors.initials: R
authors.lastname: Pratap
authors.forename: Brajendra
authors.initials: B
authors.lastname: Tripathi
authors.forename: A K
authors.initials: AK
authors.lastname: Srivastava
authors.forename: P R
authors.initials: PR
authors.lastname: Maulik
authors.forename: Vishnu Ji
authors.initials: VJ
authors.lastname: Ram
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis / Q000494:pharmacology*; D015394:Molecular Structure; D017027:Protein Tyrosine Phosphatases / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D006841:Hydrocarbons, Aromatic; D017027:Protein Tyrosine Phosphatases