Quinoline–Pyrimidine Monoazo Dye Hybrids: Synthesis, Catalyst Optimization, Molecular Docking and ADMET Studies, Biological Activity, and Dye Ability Assessment

In order to develop motifs with the potential applications as drugs and dyes, a series of novel quinoline–pyrimidine monoazo hybrids have been synthesized via the Biginelli reaction followed by diazo coupling. Molecular docking study of the synthesized compounds was performed against Topoisomerase IV from E. coli K-12 and CYP51 from C. albicans . The ADMET properties of the synthesized compounds were also investigated in order to understand the efficacy of drug candidates. The compounds bearing naphthol and orcinol substitutions showed excellent antifungal and antibacterial properties. The α-naphthol derivative displayed the highest binding affinity score (8.46 against Topoisomerase IV and 7.50 against CYP51) and an acceptable drug score (0.53) in toxicological and pharmacokinetics studies. The orcinol derivative showed a very good docking score but a low drug score in the ADMET study. Additionally, the dye ability of the synthesized compounds was assessed by dyeing cotton and silk fabrics. The compound containing a paracetamol moiety displayed excellent performance in terms of color and rubbing fastness and is promising for use in the textile industry for dyeing clothes.