Novel oxazolones incorporated azo dye: Design, synthesis photophysical-DFT aspects and antimicrobial assessments with In-silico and In-vitro surveys

• Published in: Journal of photochemistry and photobiology Vol. 7; p. 100032
• Main Authors: Albelwi, Fawzia F., Al-anazi, Menier, Naqvi, Arshi, Hritani, Zainab M., Okasha, Rawda M., Afifi, Tarek H., Hagar, Mohamed
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-09-2021; Elsevier
• Subjects: Antimicrobial assessment; DFT approaches; Molecular docking; Oxazolones azo dye; UV-visible studies; UV-visible studies; Antimicrobial assessment; Oxazolones azo dye; Molecular docking; DFT approaches
• ISSN: 2666-4690; 2666-4690
• DOI: 10.1016/j.jpap.2021.100032

•Novel oxazolone based azo dyes with new methodology are prepared and characterized.•UV–vis studies have been performed for the dyes and azo oxazolone derivatives.•A detailed study of the tautomerism of the prepared dyes has been executed through the theoretical DFT calculations.•In-vitro antifungal and antibacterial activities were evaluated for oxazolone azo dyes.•In-silico prediction methodology of all the synthesized compounds were contrasted with their biological activity results.
New derivatives of the oxazolone compounds 4(a-j) and (7a-e) containing azo dye moieties have been prepared via the Erlenmeyer reaction of their azo dye precursors. The characterization of all the synthesized compounds was confirmed by the FT-IR, 1HNMR 13CNMR and MS spectroscopic techniques. The UV-visible examination of the new molecules revealed λmax values in the range of 392–464 nm, depending on the coupling component as well as the various substituents of the benzaldehyde derivatives. All the new chromophores demonstrated an acid chromism behavior, which impacted their usage as potential acid sensors. A detailed study of the azo and hydrazo tautomerism of the prepared dyes 3a-c has been executed through the theoretical DFT calculations. Moreover, the energy levels of the FMOs and their energy difference were predicted by the DFT for all the synthesized molecules to be affected by the geometrical isomerism along with the type of the couplers. These data were employed to elucidate the UV–visible spectral measurements. Furthermore, a detailed study of the substituent effect on the UV absorbance has been achieved by the quantitative structural-activity relationship of the prepared compounds 4f-g and 7a-e. The oxazolone azo dyes were evaluated for their in-vitro antifungal and antibacterial activities and displayed potency in comparison with the reference drugs. Furthermore, the in-silico prediction methodology was contemplated for foretelling the physicochemical, drug likeliness, and ADME traits of all the synthesized compounds, where their respective docking scores were contrasted with their biological activity results.
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