Synthesis and antidiabetic activity of some new chromonyl-2,4-thiazolidinediones.

A series of chromonyl-2,4-thiazolidinediones (VIa-f) and chromonyl-2,4-imidazolidinediones (VIIa-f) was prepared by Knoevenagel reaction of substituted benzyl-2,4-thiazolidinediones (IVa-f) and substituted benzyl-2,4-imidazolidinediones (Va-f) with chromone-3-carboxaldehyde (I). The prepared compounds were tested for their insulinotropic activities in INS-1 cells. Compounds VIa, VIb, VId and VIIe (at lower concentration; 1 microg/ml) were able to increase insulin release in the presence of 5.6 mmol/l glucose; their effects were lower than that of glibenclamide (CAS 10238-21-8). The activity of the most potent compound (VId) was still 9% less than that of glibenclamide.