Thiazolidin-4-one and thiazinan-4-one derivatives analogous to rosiglitazone as potential antihyperglycemic and antidyslipidemic agents

A number of thiazolidin-4-one and thiazinan-4-one derivatives were prepared by three component condensation in one pot reaction method. These compounds were evaluated for anti-hyperglycemic activity by in vitro and in vivo assay systems. The compounds with thiazolidin-4-one and thiazinan-4-one moieties exhibited significant anti-hyperglycemic activity. A few compounds (3a, 3b, 4a and 4b) have exhibited both anti-hyperglycemic and anti-dyslipidemic activities. Among them the thiazinan-4-one derivative 4a showed maximal (45%) improvement in oral glucose tolerance test in db/db mice at 30 mg/kg oral dose.

Graphical abstractA series of thiazolidine-4-one and thiazinan-4-one are reported with promising anti-hyperglycemic activity both in vitro and in vivo models. The thiazinan-4-one derivative 4a showed maximal (45%) improvement in oral glucose tolerance test in db/db mice at 30 mg/kg oral dose.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A convenient synthesis of thiazolidinediones and thiazenans is described. ► Structural analogs of rosiglitazone as novel insulin sensitizers. ► The compounds exhibited promising antihyperglycemic and lipid lowering activity. ► In vitro and in vivo assay results are described.