Synthesis of Some New Quinazolin-4(3h)-One Derivatives and Study of Their Some Antibacterial Activity

Abstract

In this work, 2-phenyl-4(3H)-3,1-benzoxazinone (1) was synthesized from benzoylation with simultaneous cyclization of anthranilic acid and benzoyl chloride. Compound 1 was treated with hydrazine hydrate to yield 3-amino-2-phenyl-4(3H)-quinazolinone (2). Reaction of compound 2 with aromatic aldehydes/ketones resulted Schiff bases 3-6. Furthermore, treated of compound 1 with thiosemicarbazide yield compound 7, which on reaction with chloroacetic acid in the presence of sodium acetate gave 3-[(4-oxo-1,3-thiazolidin-2-yliden)amino]-2-phenylquinazolin-4(3H)-one (8). On the other hand, 2-substitutedquinazolin-4(3H)-one (9-12) were also synthesized from the reaction of anthranilic acid with different substituted amides in acetic acid. All newly synthesized compounds were characterized using different methods of spectroscopy such as IR, 1 H-NMR and 13 C-NMR. The antibacterial activity of all of the synthesized compounds was also reported. All synthesized compounds have been found to be active against both Grampositive and Gram-negative bacteria but compounds 4 and 8 were the most active one.

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

“…Amino group in anthranilic acid acts as a nucleophile and attacks to carbonyl group of urea to produce the intermediate upon elimination of ammonia group. Simultaneous nucleophilic attacks of amino group in urea resulted in the production of the product 2 upon elimination of water molecule ( 33 34 ). Chlorination reaction was performed with POCl3 to form intermediate 3 .…”