| Summary: | In this study, we synthesized benzodioxol carboxamide derivatives and investigated their antidiabetic potential. The synthesized compounds (<b>Ia-Ic</b> and <b>IIa-IId</b>) underwent characterization via HRMS, <sup>1</sup>H-, <sup>13</sup>CAPT-NMR, and MicroED. Their efficacy against α-amylase was assessed in vitro, while MTS assays were employed to gauge cytotoxicity across cancer and normal cell lines. Additionally, the antidiabetic impact of compound <b>IIc</b> was evaluated in vivo using a streptozotocin-induced diabetic mice model. Notably, <b>IIa</b> and <b>IIc</b> displayed potent α-amylase inhibition (IC<sub>50</sub> values of 0.85 and 0.68 µM, respectively) while exhibiting a negligible effect on the Hek293t normal cell line (IC<sub>50</sub> > 150 µM), suggesting their safety. Compound <b>IId</b> demonstrated significant activity against four cancer cell lines (26–65 µM). In vivo experiments revealed that five doses of <b>IIc</b> substantially reduced mice blood glucose levels from 252.2 mg/dL to 173.8 mg/dL in contrast to the control group. The compelling in vitro anticancer efficacy of <b>IIc</b> and its safety for normal cells underscores the need for further in vivo assessment of this promising compound. This research highlights the potential of benzodioxol derivatives as candidates for the future development of synthetic antidiabetic drugs.
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