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Continuous flow technology has been exploited for the generation of bicyclic pyrazolines via photo-click reactions. These heterocyclic compounds are characterized by a valuable 3D scaffold and a polar succinimide moiety. Subsequent antimicrobial testing has revealed that the incorporation of halogenated moieties, such as chlorine atoms and trifluoromethoxy groups, enhances the potency of these bacteriostatic agents, with low minimal inhibitory concentration values in the range of 0.5–4 μg mL⁻¹ being achieved.