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Synthesis of spiro acenaphthylene pyrrolizidine and pyrrolidine compounds via 1,3-dipolar cycloaddition in ionic liquid and the investigation of their biological activity as potent α-glucosidase inhibitors
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DOI：10.1016/j.jil.2026.100187.png)
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Abstract
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A new series of spiroacenaphthylene pyrrolizidine and pyrrolidine derivatives was synthesized via 1,3-dipolar cycloaddition of acenaphthoquinone with sarcosine or L-proline and various chalcone derivatives in the ionic liquid [Bmim]Br under ultrasonic irradiation at room temperature, with yields of up to 98 % within 30 min. All compounds were fully characterized and evaluated for their alpha-glucosidase inhibitory activity. Most derivatives showed inhibitory activity, with IC50 values ranging from 32.0 f 0.3 to 463.4 f 1.2 mu M, showing lower IC50 values than acarbose (IC50 = 750.0 f 1.5 mu M). Notably, compound 4k, bearing a 4-nitro substituent, had the lowest IC50 value (32.0 f 0.3 mu M), suggesting favorable interactions with the enzyme active site. These findings highlight the relevance of spiroacenaphthylene scaffolds as non-glycosidic alpha-glucosidase inhibitors and demonstrate the utility of ionic liquids for rapid and sustainable heterocyclic synthesis, which may provide a basis for future in vivo and pharmacokinetic studies.
Keywords:
Anti-diabetic drug
alpha-glucosidase inhibitor
Ionic liquid
1,3-dipolar cycloaddition
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