Synthesis of 6-oxopyrimidin-1(6H)-yl benzamide derivatives and evaluation of their antibacterial and cytotoxic activity

Design, Synthesis, and Antimicrobial Activity of Novel 6-Oxopyrimidin-1(6H)-yl Benzamide Derivatives

“…The recently synthesised oxadiazole 1 [13] upon reaction with diethylethoxy methylene malonate gave diester 2 in 88% yield. Heating of compound 2 at 260-270°C led to pyrimidone oxadiazole 3 (yield 92%), which was subjected to ring opening [13] by using various amines 4a-4j in the presence of K 2 CO 3 to afford the corresponding amino pyrimidone carboxylates 5a-5j in high yields (71-85%). Upon hydrolysis of compounds 5a-5j the corresponding acids 6a-6j were accumulated and characterized by IR, NMR, and mass spectra.…”

“…The newly synthesized dihydropyrimidine-5-carboxylic acids (6a-6j) were coupled with cyclopropyl amine following the traditional procedure, which led to the title compounds 8a-8j (Scheme 1). The structures of 8a-8j were elucidated from IR, 1 H, and 13 C NMR, and mass spectral data. 1 H NMR spectrum of the representative compound 8e demonstrated a singlet at 11.16 ppm of the amide NH proton.…”

“…The structure-activity relationship analysis indicated that, as a trend, the presence of cyclic moieties like cyclo propyl, furan, pyran, pyrrolidine, piperidine, and morpholine on the pyrimidine ring of the products resulted in larger zones of inhibition than the compounds with acyclic groups like ethanolamine, 2-methyl amine, propyl amine, and isobutyl amine. 13 C NMR spectra were measured on a Bruker AVANCE-400 spectrometer using DMSO-d 6 as a solvent and TMS as an internal standard. Mass spectra were measured on a Shimadzu GCMS-QP 1000 spectrometer.…”

“…br.s (1H). 13 Synthesis of compounds 6a-6j (general procedure). Mixture of a solution of an ester 5 (1.0 mmol) in THF-H 2 O (5 mL) with LiOH (3.0 mmol) was stirred at ambient temperature for 2 h. The reaction was monitored by TLC.…”

“…In continuation to our prior studies [13] of synthesis of 6-oxopyrimidin-1(6H)-yl benzamide derivatives, we constructed new hydrophilic 6-oxopyrimidones containing amino carboxylates. Their antimicrobial activity is tested.…”