Two series of heterocyclic analogues were synthesized from substituted chalcones (C1-5) which was prepared by reaction of acetophenone (a) and aromatic aldehydes (b1-5). One series of N-phenyl pyrazoline derivatives (K1-K5) were synthesized by reaction of chalcones (C1-5) with phenyl hydrazine in acidic medium. Another series of 3,4-dihydropyrimidine-2-one derivatives (K6-K10) were synthesized by reaction of chalcones (C1-5) with ethanolic urea in alkali medium. The yield of the synthesized compounds ranged from 62-76%. The In-vitro antidiabetic screening was performed by non enzymatic glycosylation of haemoglobin assay, α-amylase enzyme inhibition assay, α-Glucosidase enzyme inhibition assay methods. The result of all heterocyclic analogues (K1-K10) indicates that have pronounced potency when compared to standard drugs. Among that analogues K1 & K6 showed nearly equal action and analogues K2 & K7 also showed appreciable activity when compared to the standard drugs at 50μg/ml, 100μg/ml, and 150μg/ml tested concentrations.