Synthesis and antimicrobial activity of pyrazolyl-quinazolin-4(3H)ones
By Navin B. Patel, Jaymin C. Patel, Gaman G. Barat
A series of 2-[2-(2,6-dichlorophenyl)amino]benzyl-3-(5-substituted phenyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl-amino)-6-iodoquinazolin-4(3H)ones 6a-m were synthesized from 2-[2-(2,6-dichlorophenyl)amino]phenyl acetyl chloride 1 by literature procedure, involved various steps. Acid chloride 1 on cyclization reaction with 5-iodoanthranilic acid yielded 2-[2-(2,6-dichlorophenyl)amino]benzyl-6-iodo-3,1-benzoxazin-4(3H)one 2, which on reaction with hydrazine hydrate and then with acetyl chloride afforded 2-[2-(2,6-dichlorophenyl)amino]benzyl-3-acetamido-6-iodoquinazolin-4(3H)one 4. The chalcones 5a-m were synthesized by the condensation of compound 4 with different substituted aromatic aldehydes. Finally the reaction of chalcones 5a-m with phenyl hydrazine yielded the title compounds 6a-m. The structures of these compounds have been elucidated by elemental analyses, IR and NMR spectral data. The title compounds pyrazolyl-quinazolin-4(3H)ones 6a-m were evaluated for their antibacterial and antifungal activities.
Keywords : Quinazolin-4(3H)one, chalcone, pyrazole, antimicrobial activity