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. 2025 Nov 17;15(52):44749-44765.
doi: 10.1039/d5ra07614e. eCollection 2025 Nov 11.

Synthesis and characterization of novel quinazolinone-based azo disperse dyes: molecular docking, ADMET, in vitro, and dyeing performance on polyester fabric

Ahmed A Noser  1   2 , Abdulrahman A Almehizia  3 , Mohamed A Al-Omar  3 , Faris Ibrahim Alrayes  3 , Mohanad Mousa Kareem  4 , Khadra B Alomari  5 , Maha Ali Aljowni  6 , Seham A Ibrahim  1
Affiliations

Synthesis and characterization of novel quinazolinone-based azo disperse dyes: molecular docking, ADMET, in vitro, and dyeing performance on polyester fabric

Ahmed A Noser et al. RSC Adv. .

Abstract

A series of new azo quinazolinone disperse dyes was synthesized and characterized using various spectroscopic techniques. The synthetic azo dyes were applied to polyester fabrics, and their multifunctional properties, such as fastness, color assessment, dye exhaustion, fixation, pH effect, color strength, dyeing time, and dye concentration, were studied and yielded reasonable results, indicating the dyes' effectiveness in dyeing polyester. Additionally, the UV protection factor of the dyes was evaluated; results showed that these dyes provide excellent UV protection. The mode of action of these compounds was also examined both in silico through molecular docking and in vitro to assess their potential antimicrobial properties. Furthermore, ADMET pharmacokinetics were analyzed. The experimental data aligned with the molecular docking findings, which indicated that compound 5b inhibited bacterial DNA gyrase with a binding score of -10.32 kcal mol-1. Based on these results, it can be concluded that the newly synthesized dyes have strong potential in the textile dyeing industry and may be further developed.

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Conflict of interest statement

The authors have no relevant financial or non-financial interests to disclose.

Figures

Fig. 1
Fig. 1. Pharmaceutical drugs owning the quinazolines and quinazolinones structure.
Fig. 2
Fig. 2. Polyester fabric one bath dyeing profile.
Scheme 1
Scheme 1. Synthesis of compounds 2, 3.
Scheme 2
Scheme 2. Synthesis of compounds 4a–c.
Scheme 3
Scheme 3. Synthesis of compounds 5a–c.
Fig. 3
Fig. 3. Dyes 4a–c absorption spectra in different solvents.
Fig. 4
Fig. 4. Dyes 5a–c absorption spectra in different solvents.
Fig. 5
Fig. 5. Effect of solvent on absorption spectra of compound 4a–c and 5a–c.
Fig. 6
Fig. 6. Percentages of polyester fabric dye fixation and exhaustion.
Fig. 7
Fig. 7. Effect of dyeing pH on (K/S) values of polyester fabric.
Fig. 8
Fig. 8. Effect of dyeing time on (K/S) values of polyester fabric.
Fig. 9
Fig. 9. Effect of dye concentration on (K/S) values of polyester fabric.
Fig. 10
Fig. 10. UPF blocking (%).
Fig. 11
Fig. 11. Molecular docking interaction of compounds 5b and 5c against bacterial DNA gyrase.
Fig. 12
Fig. 12. Bioavailability radar plot for compound 5b and standard drugs.
Fig. 13
Fig. 13. Structure–activity relation of the novel synthesized azo quinazolinone.
See this image and copyright information in PMC

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