1-Methyl-2-(2-(prop-2-yn-1-yloxy)benzylidene)hydrazine analogues were readily prepared in good yields by the reaction of 2-(prop-2-yn-1-yloxy)benzaldehydes and methyl hydrazine. The reaction tolerates a variety of substituents on the 2-hydroxybenzaldehyde to form nitro-, halo-, methoxy-, and naphthyl-substituted 1-methyl-2-(2-(prop-2-yn-1-yloxy)benzylidene)hydrazines. The in vitro antioxidant capacity measurements revealed that among all the analyzed hydrazine analogues that surpassed the Trolox standard, 1-(2-(but-3-ynyl)-5-nitrobenzylidene)-2-methylhydrazine had the maximum value, which was approximately 1.7 times that of Trolox.