Synthesis of Pyrimidine Derivatives and Investigation of their Antimicrobial Activity

Abstract

The research work was involved in an efficient procedure for the attachment of 4- amino acetophenone with benzaldehyde in the presence of 10% NaOH to produce 1-(4-Aminophenyl)-3-phenyl-propenone (I) or arylidine acetophenone. 4-{1-[(2,4-Dinitro-phenyl)-hydrazono]-3-phenyl-allyl}-phenylamine (II) has been synthesized by the reaction of 2,4 DNP with 1-(4-Amino-phenyl)-3-phenyl-propenone. Reaction of barbituric acid with arylidine acetophenone under refluxing condensation using 50% aqueous ethanol which on further reflux to give the corresponding pyrimidine derivatives, 7-(4-Amino-phenyl)-5-phenyl-1, 5-dihydro-pyrano [2, 3-d] pyrimidine-2, 4-Dione (III). The structures of the synthesized compounds were characterized by their IR, NMR spectral data. The antibacterial and antifungal activity of the compounds was also investigated. The antimicrobial activity of the compounds at concentration at 300μg/disc was performed against three gram-positive bacteria (Bacillus cereus, Staphylococcus aureus and Listeria monocytogenes) and three gramnegative bacteria (Escherichia coli, Salmonella typhimurium, and citobacteria frundi) by Kirby-Bauer disc diffusion method using Ciprofloxacin as standard. Antifungal screening was carried out against one fungi ( Tricodarma harzianum) using Michonazole as standard. Compound I, 1-(4-Amino-phenyl)-3-phenyl-propenone exhibits no activity against the tested bacterial strains but showed moderate activity against the tested fungi Trichoderma harziniaum having inhibition zone 11 mm. Compound III, 7-(4-Amino-phenyl)-5-phenyl- 1,5-dihydro-pyrano[2,3-d] pyrimidine-2,4-Dione exhibits broad spectrum activity against both gram negative and gram positive strains tested except Listeria monocytogenes. Also the compound II, 4-{1-[(2,4-Dinitro-phenyl)-hydrazono]-3-phenyl-allyl}-phenylamine showed promising antibacterial activity having inhibition zone of 24 mm against Ctirobacteria freundi having no antifungal activity. Those bacteria revealed the zone of inhibition were 11-24 mm. The presence of an amino and unsaturated ketone function in synthesized compound may be responsible for their antibacterial and antifungal activity.