Benzoxazolyl linked benzylidene based rhodanine and analogs as novel antidiabetic agents: synthesis, molecular docking, and in vitro studies

Benzoxazolyl linked meta- and para-substituted new chemical entities (5a-5h) featuring thiazolidinedione, rhodanine, hydantoin, and thiohydantoin moieties were synthesized and characterized by H-1 NMR, C-13 NMR, FT-IR, and HRMS spectral studies. In addition, all compounds were screened for alpha-glucosidase inhibitory activity and further supported by molecular docking studies carried out at the active site of alpha-glucosidase (PDB code: 3TOP) in comparison to acarbose used as a standard drug. Out of eight tested compounds, 5d was found as the most active inhibitor of alpha-glucosidase (IC50 = 9.48 +/- 0.36 mu M), having rhodanine moiety substituted at meta-position of the phenyl ring. [GRAPHICS] .

Automated summary

Benzoxazolyl linked meta- and para-substituted chemical entities showed promising alpha-glucosidase inhibitory activity with 5d being the most active compound.