The discovery during the 1930s that a dihydropyridine (dihydronicotinamide derivative,
NADH), “hydrogen-transferring coenzyme” consequently became important in biological system, has generated numerous studies on the biochemical properties of dihydropyridines and their bioisosteres dihydropyrimidines. The search for more suitable preparation of tetrahydropyrimidinones continues today. The chemical structure of pyrazinamide provides a most valuable molecular template Ibrutinib cell line for the development of agents able to interact with a wide variety of biological activities . Tetrahydropyrimidines are structurally similar to dihydropyrimidines. Hence, it was thought worthwhile to synthesize new congeners by incorporating pyrazinamide with 1,2,3,4-tetrahydropyrimidinones moieties in a single molecular framework and to evaluate their acetyl and butyl cholinesterase inhibitor activity. All chemicals were supplied by E. Merck (Germany) and SD fine chemicals (India). Melting points were determined by the open tube capillary method and are uncorrected. The purity of the compounds was checked on thin layer chromatography (TLC) plates (silica–gel G) in the solvent system, ethanol, chloroform, Enzalutamide purchase ethyl acetate (6:2:2); the spots were located under iodine vapors or UV light. IR spectrum was obtained on a PerkinElmer
1720 FT-IR spectrometer (KBr Pellet). 1H NMR spectra were recorded or a Bruker DRX-300 (300 MHz FT-NMR) spectrometer using DMSO-d6 as solvent and TMS as internal standard. Mass spectra were obtained using Shimadzu LCMS 2010A under ESI ionization technique. Elemental analyses (C, H, and N) were performed on PerkinElmer model 240C analyzer. Pyrazinamide 1 (0.01 M) and ethyl acetoacetate Dapagliflozin 2 (0.01 M) were mixed in presence 10 ml of glacial acetic acid and refluxed for approximately 3.0 h. The colorless liquid formed was then heated on a water bath to remove the alcohol formed during the reaction.
After allowing the reaction mixture to cool, crude crystals were obtained. Purification was performed by stirring crude crystals with cold diethyl ether for approximately 20 min using a mechanical stirrer. Allowing it to stand for 15 min, followed by filtration, resulted in the third compound in a pure form of N-(3-oxobutanoyl)pyrazine-2-carboxamide 3. The mixture of N-(3-oxobutanoyl)pyrazine-2-carboxamide (0.005 M), urea/thiourea (0.0075 M), and appropriate aldehyde (0.005 M) with a catalytic amount of laboratory made p-toluenesulfonic acid in 10 ml of ethanol was subjected to microwave irradiation (300 W) for 12 min at the interval of 10 s. The reactions were monitored through TLC using the appropriate solvent system.