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

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 st...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2020-06, Vol.25 (13)
Main Authors: Tumosienė, Ingrida, Kantminienė, Kristina, Klevinskas, Arnas, Petrikaitė, Vilma, Jonuškienė, Ilona, Mickevičius, Vytautas
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antioxidants - chemistry
Antioxidants - pharmacology
Biphenyl Compounds - chemistry
Biphenyl Compounds - pharmacology
Cell Line, Tumor
Cell Proliferation - drug effects
Free Radical Scavengers - chemical synthesis
Free Radical Scavengers - chemistry
Free Radical Scavengers - pharmacology
Glioblastoma - drug therapy
Humans
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Structure
Picrates - chemistry
Picrates - pharmacology
Structure-Activity Relationship
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Summary: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, H-, C-NMR spectroscopy and mass spectrometry data. The antioxidant activity of the synthesized compounds was screened by DPPH radical scavenging method. The antioxidant activity of -(1,3-dioxoisoindolin-2-yl)-3-((4-methoxyphenyl)amino)propanamide and 3-((4-methoxyphenyl)amino)- -(1-(naphthalen-1-yl)-ethylidene)propanehydrazide has been tested to be . 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 -1,2,4-triazol-3-yl)thio)ethanone has been identified as the most active compound against the glioblastoma U-87 cell line.
ISSN:1420-3049
DOI:10.3390/molecules25132980