Diverse acyclic and cyclic g-pyridinyl amines derivatives were easily de novo prepared once more using respective aldimines derived from commercially available g-pyridine carboxyaldehyde and anilines. Obtained secondary amines were tested as possible antioxidant agents with acetylcholinesterase (AChE) inhibitory activity. Both types of amines exhibited a good antioxidant activity and moderate AChE inhibitory properties. Two compounds 4-methoxy-N-(pyridin-4-ylmethyl) aniline 3c and 4-methyl-2-(pyridin-4-yl)-1,2,3,4-tetrahydroquinoline 5a, showed highest the Trolox® Equivalent Antioxidant Capacity (TEAC) values (TEAC = 1.896 and 1.252, respectively), superior than those of α-tocopherol, well-known antioxidant (TEAC = 0.888). The best AChE inhibitor with IC₅₀ of 48.3 µM (8.9 µg/mL) was the N-(pyridin-4-ylmethyl) aniline. From comparative antioxidant/AChE tests, it was identified the 4-methoxy-N-(pyridin-4-ylmethyl) aniline 3c with suitable bio-parameters for design and development of new pyridine-based molecules with dual activity, antioxidant/AChE inhibitory capacities.