Synthesis, X-ray diffraction analysis, quantum chemical studies and <i>α</i> -amylase inhibition of probenecid derived <i>S</i> -alkylphthalimide-oxadiazole-benzenesulfonamide hybrids

Abstract

Sulphonamide and 1,3,4-oxadiazole moieties are present as integral structural parts of many drugs and pharmaceuticals. Taking into account the significance of these moieties, we herein present the synthesis, single-crystal X-ray analysis, DFT studies, and <i>α</i>-amylase inhibition of probenecid derived two <i>S</i>-alkylphthalimide-oxadiazole-benzenesulfonamide hybrids. The synthesis has been accomplished in high yields. The final structures of both hybrids have been established completely with the help of different spectro-analytical techniques, including NMR, FTIR, HR-MS, and single-crystal X-ray diffraction analyses. In an effort to confirm the experimental findings, versatile quantum mechanical calculations and Hirshfeld Surface analysis have been performed. <i>α</i>-Amylase inhibition assay has been executed to investigate the enzyme inhibitory potential of both hybrids. The low IC₅₀ value (76.92 ± 0.19 μg/mL) of hybrid <b>2</b> shows the good <i>α</i>-amylase inhibition potential of the respective compound. Ultimately, the binding affinities and features of the two hybrids are elucidated utilising a molecular docking technique against the <i>α</i>-amylase enzyme.