Abstract
A novel derivative of pyrimidine containing the 1,2,4-triazolo[1,5-a]pyrimidine ring has been synthesized by means of a condensation reaction of 3-amino-1,2,4-triazole with 4-hyroxy-6-methyl-pyran-2-one. The resulting structure of 2-(4-vinylbenzyl)-2-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-3-(4-vinylphenyl)propanoate, C10H12N4O2, (3), has been characterized by X-ray single crystal diffraction (XRD) and a variety of selected spectroscopic techniques (1H NMR, 13C and IR). The geometrical parameters and spectral data of 3 were also compared with those of a DFT geometry optimization and molecular orbital calculation utilizing the B3LYP/6-31 + G(d,p) level of theory in PCM. The intermolecular contacts in 3 were then investigated by analysis of its Hirshfeld surface along with ESP maps. The antibacterial activity of 3 against Gram positive and Gram-negative microbial strains such as Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa were evaluated with results showing antibacterial activity of 3 with respect to a MIC reference.
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•Synthesis of a novel derivative of 1,2,4-triazolo[1,5-a]pyrimidine derivative.•3D molecular structure is characterized using x-Ray and spectroscopic techniques.•Good correlations are obtained between the spectra and Xx-ray data with the predicted ones.•The synthesized compound shows significant antibacterial activity.