New Azo Disperse Dyes Based on 1H-Phenanthro[9,10-d]imidazole: Synthesis, Antibacterial Activity, ADME Study, and Molecular Docking

Abstract New azo disperse dyes 1 H -phenanthro[9,10- d ]imidazoles based on 9,10-phenanthrenequinone nucleus ( D1–D3 ) have been synthesized. The reaction of 9,10-phenanthrenequinone with 4-methoxy-benzaldhyde produced 2-(4-methoxyphenyl)-1 H -phenanthro [9,10- d ] imidazole ( A ) which next was coupled with different diazonium salts of 2-chloro-4-nitroaniline, 2-aminophenol, and 1-aminoanthraquinone to give the newly azo disperse dyes ( D1–D3 ). The structures of the synthetic dyes were established by applying elemental analyses, in addition to spectral techniques, including FTIR, 1 H NMR, 13 C NMR, and GC/EI-MS. The synthesized dyes were employed on polyester and nylon fabrics with dyeing high-temperature and pressure techniques. The K/S values and UPF were measured. The fastness properties of the dyed fabrics using D–D3 exposed auspicious color fastness toward (light, rubbing, washing, and perspiration fastness). The testified dyes promoted higher antibacterial efficacies on nylon 6 and polyester fabrics versus Escherichia coli (Gram-negative bacterium) and Staphylococcus aureus (Gram-positive bacterium). The mechanism of antibacterial activity was suggested to be by action of D1–D3 against E. coli Lgt complexing with phosphatidylglycerol (PDB: 5AZB) that co-crystalized with the native ligand (palmitic acid). Also, some physicochemical, pharmacokinetic parameters, and drug-likeness (ADME) were achieved.