Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives

Abstract

A series of novel 4-anilinoquinazoline derivatives were designed and synthesized from benzoic acid through ring closure, chlorination or nucleophilic substitution. The structures of compounds were characterized by IR, ¹H-NMR and mass spectroscopy. All synthesized derivatives were screened for their antimicrobial activities against Gram-positive (<i>Staphylococcus aurous</i>, <i>Bacillus subtilis</i>, <i>Listeria monocitogenes</i>) and Gram-negative (<i>Escherichia coli</i>, <i>Pseudomonas aeruginosa</i>, <i>Salmonella entritidis</i>) bacteria and also for antifungal activities against <i>Candida albicans</i> using the conventional micro dilution method. Most of the compounds have shown good antibacterial activities, especially compound <b>4c</b> having highest activities against <i>E. coli</i> at 32 μg/mL concentration while the tested compounds did not exhibited remarkable antifungal activities. The potential DNA gyrase inhibitory activity of these compounds was investigated <i>in silico</i> using molecular docking simulation method. All compounds showed good results especially compound <b>4c</b> which showed the lowest ΔG_bind results (-8.16 Kcal/mol).