Synthesis and Characterization of 5-pentadecyl-2.4-thiazolidinedione and 4-4'-(ethane-1,2-diylbis(oxy))dibenzonitrile

The promising activity of thiazolidinediones has made it an attractive molecular feature in the development of new derivatives aimed to exhibit pharmacological significance. Thiazolidinedione-derived medicines are highly potent drugs for the treatment of diabetes mellitus type II (T2DM); it is known for its remarkable anti-hyperglycemic and insulin sensitizing property. Research shows that modification of the substituents on the thiazolidine-2,4-dione (TZD) moiety may lead to a plethora of beneficial biological activities. In this study, a derivative of TZD, 5- pentadecylthiazolidine-2,4-dione, containing a 15-carbon alkyl chain was prepared. The preparation involves the bimolecular nucleophilic substitution (SN2) reaction of thiazolidine-2,4-dione and pentadecyl bromide with piperidine base and tetrahydrofuran as solvent. The product was obtained as white powder with a melting point of 54-55°C in 9.8 % yield. The compound will hopefully show greater potency and less adverse side effects relative to the anti-T2DM drugs present in the market. The compound was characterized using thin layer chromatography, melting point determination, and mass spectrometry.