Antioxidant and Anticancer Activity of Novel Derivatives of 3-[(4-Methoxyphenyl)amino]propane-hydrazide

• Main Authors: Ingrida Tumosienė, Kristina Kantminienė, Arnas Klevinskas, Vilma Petrikaitė, Ilona Jonuškienė, Vytautas Mickevičius
• Format: Article
• Language: English
• Published: MDPI AG 2020-06-01
• Series: Molecules
• Subjects: hydrazine; Schiff base; 1,2,4-triazole-3-thione; antioxidative; anticancer
• Online Access: https://www.mdpi.com/1420-3049/25/13/2980

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 <i>N</i>-(1,3-dioxoisoindolin-2-yl)-3-((4-methoxyphenyl)amino)propanamide and 3-((4-methoxyphenyl)amino)-<i>N'</i>-(1-(naphthalen-1-yl)-ethylidene)propanehydrazide has been tested to be <i>ca</i>. 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-4<i>H</i>-1,2,4-triazol-3-yl)thio)ethanone has been identified as the most active compound against the glioblastoma U-87 cell line.