Series of novel 3-[(4-methoxyphenyl)amino]propanehydrazide derivatives bearing semicarbazide, thiosemicarbazide, thiadiazole, triazolone, triazolethione, thiophenyltriazole, furan, thiophene, naphthalene, pyrrole, isoindoline-1,3-dione, oxindole, etc. moieties were synthesized and their molecular structures were confirmed by IR, 1H-, 13C-NMR spectroscopy and mass spectrometry data. The antioxidant activity of the synthesized compounds was screened by DPPH radical scavenging method. The antioxidant activity of N-(1,3-dioxoisoindolin-2-yl)-3-((4-methoxyphenyl)amino)propanamide and 3-((4-methoxyphenyl)amino)-N'-(1-(naphthalen-1-yl)-ethylidene)propanehydrazide has been tested to be ca. 1.4 times higher than that of a well-known antioxidant ascorbic acid. Anticancer activity was tested by MTT assay against human glioblastoma U-87 and triple-negative breast cancer MDA-MB-231 cell lines. In general, the tested compounds were more cytotoxic against U-87 than MDA-MB-231 cell line. 1-(4-Fluorophenyl)-2-((5-(2-((4-methoxyphenyl)amino)ethyl)-4-phenyl-4H-1,2,4-triazol-3-yl)thio)ethanone has been identified as the most active compound against the glioblastoma U-87 cell line.
Keywords: 1,2,4-triazole-3-thione; Schiff base; anticancer; antioxidative; hydrazine.