Background and purpose: Carbohydrate hydrolysis enzymes including α-glucosidase and α-amylase are related to type 2 diabetes mellitus. The inhibiting of these enzymes might use for type 2 diabetes mellitus treatment. Experimental approach: N-substituted-acetylpyrrolidine linked with -benzyl- (N-(benzyl)-2-acetylpyrrolidine (4a)) and -tosyl- (N-(tosyl)-2-acetylpyrrolidine (4b)) were synthesized and evaluated for their pharmaceutical properties against a-glucosidase and a-amylase and free radical scavenging activity. The structures of 4a and 4b were determined through spectral studies (1H-NMR). Findings / Results: Both compounds 4a and 4b had highest inhibitory potential on a-glucosidase with the IC50 values of 0.52 ± 0.02 and 1.64 ± 0.08 mM, respectively. The kinetic investigation of 4a and 4b against a-glucosidase and a-amylase were functioned in mixed type inhibition. Moreover, both compounds are more likely to bind with the free enzyme than the enzyme-substrate complex based on the Ki < Ki’ on the a-glucosidase and a-amylase enzymes. Regarding the free radical scavenging, 4a had a higher capacity than 4b with IC50 values of 1.01 ± 0.010 mM for 4a and 1.82 ± 0.048 mM for 4b. Conclusion and implications: Our results indicated that a derivative of N-substitute-acetylpyrrolidine had high potential to inhibit a-glucosidase and a-amylase, and their free radical scavenging properties might be applied to the therapeutic care of patients with type 2 diabetes mellitus.

中文翻译：

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N-乙酰吡咯烷衍生物的合成及对α-葡萄糖苷酶和α-淀粉酶的抑制活性

背景与目的：包括α-葡萄糖苷酶和α-淀粉酶在内的碳水化合物水解酶与2型糖尿病有关。这些酶的抑制可能用于 2 型糖尿病的治疗。实验方法：合成与-苄基-(N-(苄基)-2-乙酰基吡咯烷(4a))和-甲苯磺酰基-(N-(甲苯磺酰基)-2-乙酰基吡咯烷(4b))连接的N-取代-乙酰基吡咯烷并评估其它们对α-葡萄糖苷酶和α-淀粉酶的药学特性和自由基清除活性。4a 和 4b 的结构通过光谱研究 (1H-NMR) 确定。调查结果/结果：化合物 4a 和 4b 对 α-葡萄糖苷酶的抑制潜力最高，IC50 值分别为 0.52 ± 0.02 和 1.64 ± 0.08 mM。4a和4b对α-葡萄糖苷酶和α-淀粉酶的动力学研究在混合型抑制中起作用。此外，基于α-葡萄糖苷酶和α-淀粉酶上的Ki < Ki'，这两种化合物比酶-底物复合物更可能与游离酶结合。关于自由基清除，4a 的容量高于 4b，4a 的 IC50 值为 1.01 ± 0.010 mM，4b 的 IC50 值为 1.82 ± 0.048 mM。结论和启示：我们的研究结果表明，N-取代乙酰吡咯烷衍生物具有很高的抑制α-葡萄糖苷酶和α-淀粉酶的潜力，其清除自由基的特性可能适用于2型糖尿病患者的治疗护理。与基于α-葡萄糖苷酶和α-淀粉酶的Ki < Ki'的酶-底物复合物相比，这两种化合物更可能与游离酶结合。关于自由基清除，4a 的容量高于 4b，4a 的 IC50 值为 1.01 ± 0.010 mM，4b 的 IC50 值为 1.82 ± 0.048 mM。结论和启示：我们的研究结果表明，N-取代乙酰吡咯烷衍生物具有很高的抑制α-葡萄糖苷酶和α-淀粉酶的潜力，其清除自由基的特性可能适用于2型糖尿病患者的治疗护理。与基于α-葡萄糖苷酶和α-淀粉酶的Ki < Ki'的酶-底物复合物相比，这两种化合物更可能与游离酶结合。关于自由基清除，4a 的容量高于 4b，4a 的 IC50 值为 1.01 ± 0.010 mM，4b 的 IC50 值为 1.82 ± 0.048 mM。结论和启示：我们的研究结果表明，N-取代乙酰吡咯烷衍生物具有很高的抑制α-葡萄糖苷酶和α-淀粉酶的潜力，其清除自由基的特性可能适用于2型糖尿病患者的治疗护理。