Preparation, characterization and antimicrobial properties of some s-triazine/quinazolinone hybrids

Heterocyclic structures are the basic elements of many pharmaceuticals products.The tri-substituted 1,3,5-triazine analogues is a very important pharmacophore due toits presence in an enormous amount of bioactive compounds [1-4]. In this study, a series of novel 2-methyl-3-((4-(4-arylamino)-6-(phenylamino)-1,3,5-triazin-2-yl)amino)quinazolin-4(3H)-one derivative as potential antimicrobial agents was designed and synthesized. The first chlorine group of the cyanuric chloride (CC) wasreplaced by aniline in acetic acid at 5 °C. The second chlorine group of the CC was replaced by 4-chlorobenzenamine, 4-aminobenzonitrile and sulfanilamide in thepresence of sodium acetate. The last chlorine group of the CC was replaced by hydrazine molecule. Finally, 2-methyl-4H-1,3-benzoxazin-4-one was added to the above compounds and refluxed in ethanol for 10h (Scheme 1). The chemical structure and purity of these hybrid compounds were evaluated by elemental analyses, thin layer chromatography, Fourier transform infrared and, proton along with carbon nuclear magnetic resonance techniques. Antimicrobial activity of the hybrid compounds were study by three Gram-negative bacteria and three Grampositive bacteria using the serial broth dilution method. Among them, compound with benzenesulfonamide group showed higher antimicrobial activity with a minimum inhibitory concentration (MIC) value of 16 and 32μg/mL. Furthermore, these compounds showed good activity against several tested strains.