In the pursuit of potent enzyme inhibitors to combat metabolic and microbial diseases, here we report the rational design and synthesis of novel cyclopropyl-tethered 2-iminothiazolidin-4-one-isatin hybrids (7a-k), aimed at overcoming limitations of current therapeutics in terms of potency, selectivity, and safety. The structures were confirmed through spectroscopy and compounds were assessed for inhibitory potential against α-glucosidase, urease, and Intestinal Alkaline phosphatase (IALP). Notably, compound (7d) featuring n-heptyl chain exhibited the highest potency against IALP, with an IC₅₀ value of 55.
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