Synthesis and antihyperglycemic activity of 2-(substituted phenyl)-3-{[4-(1-naphthyl)-1,3-thiazol-2-yl] amino}-4-oxo-1,3-thiazolidin-5-ylacetic acid derivatives.

The title compounds were prepared by brominating 1-acetylnaphthalene in chloroform followed by condensation with substituted benzaldehyde thiosemicarbazones using ethanol to get 4-naphthalen-1-yl-2-{2-[(substituted phenyl)methylidene]hydrazino}-1,3-thiazoles. These thiazole derivatives were then cyclized to title compounds by reacting with thiomalic acid in dioxane using ZnCl2. All the synthesized compounds were characterized on the basis of their IR, 1H NMR, and elemental analysis. The antihyperglycemic study was divided into two phases. Phase-I involved evaluation of blood glucose lowering ability of thiazolidinones in normal rats by sucrose-loaded model (SLM). Phase-II study included the evaluation of blood sugar by alloxan model.