Extensive structure-activity relationship studies performed on sp2-iminoglycolipids revealed the fundamental role played by a linear dodecylsulfide/sulfonyl aglycone chain on the anticancer, antiparasitic and immunomodulatory activities. However, the influence of structural modifications within the glycone region on the therapeutic performance remains largely underexplored. To address this gap, we have designed and stereoselectively synthesized a novel series of sp2-iminoglycolipids incorporating targeted modifications to the glycomimetic unit. These include C2 deoxygenation, bioisosteric replacement of the hydroxyl group with fluorine, and selective installation of aromatic hydrocarbons at the O3 position. Among the synthesized compounds, the fluorinated derivative (1R)-2-deoxy-1-S-dodecyl-2-fluoro-3-O-(p-fluorobenzyl)-5N,6O-oxomethylidene-1-sulfonylnojirimycin emerged as a promising multi-target candidate. Live-cell imaging in human cervical cancer (HeLa) cells revealed phenotypic markers characteristic of apoptotic cell death. Furthermore, clonogenic assays showed a significant, concentration-dependent reduction in the formation of cancer cell colonies, indicating impairment of tumor cell reproductive viability. Altogether, these data support a potent antiproliferative activity. This compound also exhibited strong antiparasitic activity, effectively inhibiting the growth of Leishmania donovani amastigotes at low micromolar concentrations. Additionally, it showed notable anti-inflammatory properties in microglial cells by downregulating the NLRP3 inflammasome signaling pathway following inflammatory stimulation, as evidenced by reduced caspase-1 activation and suppressed IL-1β release.