Synthesis, Characterization, Antimicrobial and Anticarcinogenic Activity of Quinazoline Derivatives

Abstract

The reaction of β-dicarbonyl compounds as ethyl acetoacetate with hydrazines is a well-established route for the creation of pyrazole derivatives. In this research, 4-hydrazinoquinazoline (4) reacted with ethyl acetoacetate in boiling ethanol it gives ethyl 3-oxobutanoate quinazolin-4-yl-hydrazone (5). Cyclization of the compound (5) in the presence of glacial acetic acid is passed to form 4-(5-hydroxy-3-methyl-1H-pyrazol-1-yl)quinazoline(6). Furthermore, the reaction of phenylisothiocyanate compounds with hydrazines is a well-established way for the synthesis of tetrazinoquinazoline (8). The new compounds are confirmed by elemental analysis, nuclear magnetic resonance, infrared, and mass spectra. In-vitro anti-tumor evaluation of the new compounds across three cell lines HepG2 (liver carcinoma), HCT-116 (colon carcinoma), and MCF-7 (breast carcinoma) indicats high anti-tumor activity. In addition, antimicrobial activity of specific synthesized compounds are screened against four bacterial species. Amongst four, two Gram-negative are Escherichia coli, Pseudomonas aeuroginosa and gram-positive as Staphylococcus aureus and Bacillus subtilis. The antibacterial activity of Compounds (5) and (6) are greater comparing to standard drug (Amphicillin).