New Gemcitabine Derivatives as Potent in vitro α-Glucosidase Inhibitors

Abstract

In this work, new heterocyclic compounds 1,2,3-triazoline derivatives starting from gemcitabine were synthesized. At first, gemcitabine was converted to 2-azido gemcitabine (G) through the reaction of gemcitabine with sodium azide. 1,2,3-Triazolines were prepared from the reaction of 2-azido gemcitabine with some unsaturated compounds such as malic anhydride, cinamic acid and acryl amide by click reaction. The products were identified by Fourier-transform infrared spectroscopy (FTIR) and proton nuclear magnetic resonance (1H-NMR) technique. The α-glucosidase inhibitory activities of all the synthesized compounds were determined in vitro. All the tested compounds showed α-glucosidase inhibitory activity of IC50 = 144.8 ± 1.74, 212.9 ± 3.4 and 345 ± 4.5 μM against the α-glucosidase enzyme when compared to the standard drug acarbose IC50 = 824 ± 1.73 μM.

Keywords

• gemcitabine
• 1,2,3-triazolines
• α-glucosidase inhibitors