Synthesis, molecular modeling, ADMET and fastness studies of some quinoline encompassing pyrimidine azo dye derivatives as potent antimicrobial agents

Abstract

• Synthesized novel Quinoline-Pyrimidine entities using Biginelli reaction followed by diazotization reaction. • Structural confirmation of compounds by FTIR, 1 H NMR, 13 C NMR and Mass spectroscopy. • Naphthol substituted (3b, 3c) and Orcinol (3f) substituted compounds were act as a potential candidate for antimicrobial drug discovery from antimicrobial, molecular docking and ADMET studies. • EDG substituted cresol derivatives 3e, 3j and 3m were the most promising cotton fabric dyes with admirable fastness properties referencing gray scale. Targeting the current issue of microbial resistance and novel dye molecules for textile industries, we have synthesized a series of novel Quinoline-Pyrimidine hybrids (3a–p). The naphthol group substituted compounds were outstanding in terms of antimicrobial screening as compound 3c against E. coli, A. niger and compound 3b against C. albicans unveiled excellent inhibition activity. The docking score of 3b was highest against both Topoisomerase IV (7.87) and CYP51 (8.48) enzymes while compound 3c also had decent dock score (7.02; Topoisomerase IV and 7.98; CYP51) compared to reference drugs. In silico pharmacokinetic and toxicity prediction data revealed that compound 3c had the highest drug score (0.71) while compound 3b on the other hand displayed feeble drug score (0.39). Assessing the dyeing performance and colour as well as rubbing fastness properties on cotton and silk, it was observed that cresol derivatives 3e, 3j and 3m exhibited excellent fastness properties towards cotton fabric.