Quinoline-bearing 1,6-dihydropyrimidine azo dye derivatives: Synthesis, antimicrobial activity, molecular docking, ADMET, and dye fastness studies

Abstract

A series of novel Quinoline-Pyrimidine hybrids (3a-p) has been synthesized to address the issue of microbial resistance and provide new dye molecules for the textile industry. The compounds with naphthol group substitutions, such as compound 3c against S. aureus, E. coli and C. albicans, and compound 3b against C. albicans, showed excellent antimicrobial activity. In docking studies, compound 3b and 3c had shown the highest docking score against both Topoisomerase IV and CYP51 enzymes ranging from 8.31 to 8.55 compared to reference drugs. Additionally, in-silico pharmacokinetic and toxicity prediction data indicated that compound 3b had the highest drug score (0.73), with compound 3c close behind at 0.72. Furthermore, upon evaluating the dyeing performance and colour fastness of cotton and silk, we noticed that phenol derivatives with hydroxyl and nitro-substituted compounds (3a, 3n, 3o, and 3p) exhibited outstanding fastness properties on fabrics.