Synthesis and biological evaluation of some azo dyes based on 3-cyano-6-hydroxy-4-methyl-1-propyl-2-pyridone

Abstract

Azo dyes are the most important group of organic synthetic dyes. High molar extinction coefficients, which characterize azo compounds, contribute to their wide use in traditional dyeing of various materials, as well as the increasing application in new technologies such as optical devices and solar cells. Numerous studies show that azo dyes based on heterocyclic molecules possess biological activity. Arylazo pyridone dyes belong to the class of disperse dyes, which exhibit antibacterial, antifungal, anticancer and antioxidant properties. In this work, three azo dyes were synthesized starting from 2-, 3- and 4-aminophenol and 3-cyano-6-hydroxy-4-methyl-1-propyl-2-pyridone. The structure of dyes was confirmed by ATR-FTIR, NMR and UV-Vis spectroscopy. The antioxidant activity of compounds was examined by the ABTS method. Physico-chemical descriptors and ADME parameters were determined in silico using SwissADME program.

Azo boje su najznačajnija grupa organskih sintetskih boja. Visoki molarni ekstencioni koefici-jenti, koji karakterišu azo jedinjena, doprinose njihovoj širokoj upotrebi kako u tradicionalnom bo-jenju materijala, tako i sve većoj primeni u novijim tehnologijama kao što su optički materijali i solarne ćelije. Mnoga istraživanja pokazuju da azo boje dobijene iz heterocikličnih molekula imaju biološku aktivnost. Arilazo piridonske boje pripadaju klasi disperznih boja koje ispoljavaju antibak-terijsku, antifungalnu, antikancerogenu i antioksidativnu aktivnost. U ovom radu sintetisane su tri azo boje polazeći iz 2-, 3-i 4-aminofenola i 3-cijano-6-hidroksi-4-metil-1-propil-2-piridona. Struk-tura jedinjenja potvrđena je ATR-FTIR, NMR i UV-Vis podacima. Antioksidsativna aktivnost jedinje-nja ispitana je ABTS metodom. Fizičko-hemijski deskriptori i ADME parametari određeni su in silico pomoću SwissADME programa.