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Bis-Schiff bases 1–27 have been synthesized and their in vitro antiglycation potential has been evaluated. Compounds 21 (IC₅₀=243.95±4.59μM), 20 (IC₅₀=257.61±5.63μM), and 7 (IC₅₀=291.14±2.53μM) showed an excellent antiglycation activity better than the standard (rutin, IC₅₀=294.46±1.50μM). This study has identified a series of potential molecules as antiglycation agents. A structure–activity relationship has been studied, and all the compounds were characterized by spectroscopic techniques.