We report the synthesis and in vitro antiglycation activity of more than 80 amino acid–heterocycle conjugate derived ureas and thioureas. They were characterized by physical and spectroscopical methods. Many of the analogues synthesized showed activity at the sub-micro molar level. Introduction of different amino acids as linker and systematic variation of the substituents on the aromatic ring revealed promising leads. In particular, compounds containing Glu and Tyr as the linkers exhibited high antiglycating potency with IC50 1–4 μM as against the reference, rutin with IC50 41.9 μM. Conclusions: Compounds bearing halogen atoms emerged as the most active analogues and serve as lead for future studies.