TY - JOUR
T1 - Synthesis, crystal structure, spectroscopic characterization, hirshfeld surface analysis, DFT calculations and antibacterial activity of ethyl 2-(4-vinylbenzyl)-2-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-3-(4-vinylphenyl)propanoate
AU - Lahmidi, Sanae
AU - Anouar, El Hassane
AU - El Hamdaoui, Lahcen
AU - Ouzidan, Younes
AU - Kaur, Manpreet
AU - Jasinski, Jerry P.
AU - Sebbar, Nada Kheira
AU - Essassi, El Mokhtar
AU - El Moussaouiti, Mohammed
N1 - Publisher Copyright:
© 2019 Elsevier B.V.
PY - 2019/9/5
Y1 - 2019/9/5
N2 - 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.
AB - 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.
KW - 1,2,4-triazolo[1,5-a]pyrimidine
KW - Antibacterial activity
KW - DFT
KW - Hirshfeld surface
KW - X-ray
KW - π-stacking
UR - http://www.scopus.com/inward/record.url?scp=85064808372&partnerID=8YFLogxK
U2 - 10.1016/j.molstruc.2019.04.076
DO - 10.1016/j.molstruc.2019.04.076
M3 - Article
AN - SCOPUS:85064808372
SN - 0022-2860
VL - 1191
SP - 66
EP - 75
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
ER -