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Thiazolidinediones are well known for causing reduction in blood glucose levels. A number of thiazolidinediones have been approved for clinical use in diabetes. Present research work is based on the synthesis of thiazolidinedione derivatives that were designed previously using 2D QSAR for antidiabetic activity. Thiazolidine-2,4-diones derivatives having carboxylic ester appendages at N-3 and 5-substituted benzylidene were studied and the syntheses of only four derivatives were performed that were predicted to have promising antidiabetic activities. Their effect on hypoglycemic activity was performed using a sucrose loaded model. Compounds 5a and 5b were found to have prominent activities at 100 mg/kg by oral route administration.