In this study, we synthesized benzodioxol carboxamide derivatives and investigated their antidiabetic potential. The synthesized compounds (Ia-Ic and IIa-IId) underwent characterization via HRMS, 1H-, 13CAPT-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 IIc was evaluated in vivo using a streptozotocin-induced diabetic mice model. Notably, IIa and IIc displayed potent α-amylase inhibition (IC50 values of 0.85 and 0.68 µM, respectively) while exhibiting a negligible effect on the Hek293t normal cell line (IC50 > 150 µM), suggesting their safety. Compound IId demonstrated significant activity against four cancer cell lines (26–65 µM). In vivo experiments revealed that five doses of IIc 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 IIc 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.

中文翻译：

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作为抗糖尿病药物的新型苯并二氧杂环戊烯衍生物的表征和研究：动物模型的体外和体内研究

在这项研究中，我们合成了苯并二氧杂环戊烯甲酰胺衍生物并研究了它们的抗糖尿病潜力。合成的化合物（Ia-Ic 和 IIa-IId）通过 HRMS、1H-、13CAPT-NMR 和 MicroED 进行表征。它们对 α-淀粉酶的功效在体外进行了评估，而 MTS 测定则用于测量癌症和正常细胞系的细胞毒性。此外，使用链脲佐菌素诱导的糖尿病小鼠模型在体内评估了化合物IIc的抗糖尿病作用。值得注意的是，IIa 和 IIc 显示出有效的 α-淀粉酶抑制作用（IC50 值分别为 0.85 和 0.68 µM），而对 Hek293t 正常细胞系的影响可忽略不计（IC50 > 150 µM），表明它们的安全性。化合物 IId 对四种癌细胞系 (26–65 µM) 表现出显着的活性。体内实验表明，与对照组相比，五剂 IIc 显着降低了小鼠血糖水平，从 252.2 mg/dL 降至 173.8 mg/dL。IIc 引人注目的体外抗癌功效及其对正常细胞的安全性强调了对这种有前景的化合物进行进一步体内评估的必要性。这项研究凸显了苯并二氧杂环戊烯衍生物作为未来合成抗糖尿病药物开发候选者的潜力。