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The main objective of the present work is to design and synthesize a series of novel Z-acrylonitrile motifs and their subsequent characterization and analysis of their biological profile. The structural authentication of the newly synthesized compounds has been ascertained on the basis of IR, 1H NMR, 13C NMR, Mass Spectrometry and Elemental analysis. The first chapter embodies a critical review of literature about the advancements made in the field of acrylonitrile derivatives. The second and third chapter deals with the synthesis, characterization, optimization conditions and stereochemical aspects of the synthesized compounds. Finally, fourth and fifth chapter embodies acetylcholinesterase inhibition and density functional theory (DFT) studies, followed by materials and methods employed in the present scheme.