Synthesis, crystal structure and antibacterial properties of 6-methyl-2-oxo-4-(quinolin-2-yl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Abstract

The synthesis and investigation of a new biologically active derivative of dihydropyrimidine are reported. The structure of the synthesized compound was investigated by X-ray single crystal diffraction method. In order to understand the molecular interactions, the Hirshfeld surface and contacts enrichment analyses were performed. The crystal packing is mainly stabilized by strong N-H…O hydrogen bonds and aromatic cycle stacking. Among the different types of oxygen atoms, the most electronegative had the highest propensity to form H-bonds. Biological activity of the synthesized compound was studied against E.coli, P. aeruginosa and S. aureus bacteria.

Crystal structure, Hirshfeld surface analysis, computational and antifungal studies of dihydropyrimidines on the basis of salicylaldehyde derivatives

“…Furthermore, the plane through the four coplanar atoms (N1, C10, C8 and C7) makes a dihedral angle of 77.54° with the phenyl ring. The carbonyl, carboxylate and methyl groups, except for the H atoms, are nearly coplanar with the attached heterocyclic ring [39,54] and the bromine atom in this structure had equatorial orientation in the phenyl ring plane with torsion angles С3-С2-С1-Br1 and С5-C6-С1-Br1 equal to 179.11 (19) and -178.5°(2), respectively. The substitution of the bromo atom by the nitro group and the presence of water molecules introduce changes in the molecular conformation and crystal packing (Figure 6).…”

“…Considering their importance in pharmacy, their synthesis methods in the presence of building blocks with various functional groups are always modified by chemists in order to find a more benign, cheaper and "green" method. Along with synthesis methods, computational studies and crystal structure investigations of dihydropyrimidines are also very important, which provide key information about non-covalent interactions and their role in crystal packing, tautomerization and conformation of dihydropyrimidine ring [39][40][41] allowing delving into the structurebiological activity relationship of investigated compounds [42].…”

Synthesis, crystal structure, Hirshfeld surface, computational and antibacterial studies of a 9-phenanthrenecarboxaldehyde-based thiodihydropyrimidine derivative

“…In the present case, several catalysts including Cu(OTf)2, InCl3, InBr3, CF3COOH, Yb(OTf)3, YbCl3, HCl, H2SO4, NH4Cl, CAN, CH3COOH, CH2ClCOOH and others did not lead to the desired compound [8]. We were only able to obtain the title dihydropyrimidine by improving a literature procedure [52] and performing the reaction under microwave irradiation (Scheme 1). The structure of the newly synthesized dihydropyrimidine was determined by 1 H, 13 C NMR, mass spectrometry, and elemental analysis.…”

“…Overall, these advantages have encouraged scientists to optimize synthetic methods to produce dihydropyrimidines, searching for innovative catalysts and constructing new molecules from different building blocks by employing the Biginelli reaction. To gain a deeper insight into the stereochemistry, conformation, and non-covalent interactions between molecules, which are key factors affecting activity, various methods have been used, leading to the development, enhancement and enrichment of their chemistry [51][52][53]. Furthermore, theoretical calculations have been frequently used to predict and/or explain their activities by finding the relationship between the structure of the investigated molecule and its biological effect [54,55].…”

Synthesis, crystal structure and antibacterial studies of 2,4,6-trimetoxybenzaldehyde based dihydropyrimidine derivatives

“…Dimeric motifs utilizing N3-H3•••O1 i and C9-H9B•••O2 iii hydrogen bonds can be described R2 2 (10) graph-set motif connecting two adjacent molecules involving the carbonyl group and R2 2 (8) which involved the ketone group in polar sheets along a-axis (Fig. 5, Table S2) [75].…”