Synthesis, solvatochromism, and biological activity of novel azo dyes bearing 2-pyridone and benzimidazole moieties

Abstract

New azo dyes bearing 2-pyridone and benzimidazole moieties were prepared using diazotization of 4-(1Hbenzo[d]imidazol-2-yl)aniline and coupling of the obtained diazonium salt with substituted 3-cyano-2-pyridones. Obtained compounds were characterized via UV-Vis, FT-IR, and 1 H and 13 C NMR spectroscopy as well as by elemental analysis data. The UV-Vis spectra of the synthesized dyes were measured in thirteen solvents of different properties at room temperature. Solvatochromism and tautomerism of novel azo dyes were discussed. An MTT (3,4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) test was performed to prove the biocompatibility of the investigated dyes. The investigated dyes exhibited satisfying antiproliferative activities against both tumor cell lines, MDA-MB-231 and HCT-116, demonstrating the potent capacity for treatment of tumors.

On the azo dyes derived from benzoic and cinnamic acids used as photosensitizersin dye-sensitized solar cells

“…The existence of these bands in the FT-IR spectra confirms the hydrazone structure of dye molecules and supports the literature data [25,26]. Moreover, compounds 2b and 5b show the absence of stretching of the second carbonyl band, which would have originated from the noncarboxylic C=O group in the 1630-1700 cm −1 domain [27,28], if the mentioned azo dye molecules had been found as hydrazone tautomers. The bands at 1505 and 1503 cm −1 are assigned to -N=N-stretching vibrations for 2b and 5b, respectively [29,30].…”

Novel azo pyridone dyes based on dihydropyrimidinone skeleton: Synthesis, DFT study and anticancer activity

“…Among this class of azo dyes, those with 2-pyridone moiety in the structure are particularly significant. Besides their remarkable coloration properties [13], azo pyridone dyes exhibit antibacterial activity [14] and demonstrate the potency for cancer therapy [15]. One of the most investigated feature of azo pyridone dyes is the phenomenon of azo-hydrazone tautomerism [16][17][18].…”

Synthesis and characterization of azobenzene derived from 8-aminoquinoline in aqueous media

“…However, limitation of the natural dye sources led scientists to synthesize dyes with a wide variety of new colors. Azo dyes can be easily prepared by using diazo and coupling components that are generally low-cost materials (26). Due to remarkable stability, light resistance and easy diversification of donor and acceptor groups in the organic compounds, azo dyes are one-step ahead of other dyes (27,28).…”