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Synthesis, crystal structure and antibacterial studies of dihydropyrimidines and their regioselectively oxidized products.

ABSTRACT: The syntheses and investigations of new biologically active derivatives of dihydropyrimidines by Biginelli reaction in the presence of copper triflate are reported. Due to the fact that salicylaldehyde and its derivatives under Biginelli reaction conditions can lead to the formation of 2 types of dihydropyrimidines, the influence of copper triflate on product formation was also investigated. In addition to this, regioselective oxidation of dihydropyrimidines was performed in the presence of cerium ammonium nitrate and novel oxidized dihydropyrimidines were obtained. Single crystals of some of them were obtained and as a result, the structures of them were investigated by X-ray diffraction method, which allows determining the presence of hydrogen bonds in their structures. In addition to this, the presence of hydrogen bonds in their structures affects the formation of the corresponding tautomer during oxidizing of dihydropyrimidines. Since dihydropyrimidines are claimed to be biologically active compounds, activities of the synthesized compounds were studied against Acinetobacter baumanii, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae and Staphylococcus aureus bacteria.

SUBMITTER: Huseynzada AE

PROVIDER: S-EPMC8694924 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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Synthesis, crystal structure and antibacterial studies of dihydropyrimidines and their regioselectively oxidized products.

Huseynzada Alakbar E AE Jelch Christian C Akhundzada Haji Vahid N HVN Soudani Sarra S Ben Nasr Cherif C Israyilova Aygun A Doria Filippo F Hasanova Ulviyya A UA Khankishiyeva Rana F RF Freccero Mauro M

RSC advances 20210203 11

The syntheses and investigations of new biologically active derivatives of dihydropyrimidines by Biginelli reaction in the presence of copper triflate are reported. Due to the fact that salicylaldehyde and its derivatives under Biginelli reaction conditions can lead to the formation of 2 types of dihydropyrimidines, the influence of copper triflate on product formation was also investigated. In addition to this, regioselective oxidation of dihydropyrimidines was performed in the presence of ceri ...[more]

PMID: 35423136

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Project description:A novel Schiff base derivative of 4-aminoantipyrine, that is, (E)-4-(2-methoxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (MBA-dMPP), was synthesized and characterized by FT-IR, 1H-NMR, and EI-MS. Single-crystal X-ray diffraction data revealed MBA-dMPP adopts a trans configuration around its central C=N double bond, and forms orthorhombic crystals. XRD revealed that MBA-dMPP possess two different planes, in which the pyrazolone and benzylidene groups attached to C9 of the pyrazolone ring are almost coplanar and the phenyl ring connected to the N1 atom of the pyrazolone moiety lies in another plane. The intermolecular, host-guest C-H…O, C-H…N, and C-H…C van der Waals interactions were found to form a 3D network and confer stability to the MBA-dMPP crystal structure. The quantitative and qualitative solid state behaviors of MBA-dMPP were subjected to 3D Hirshfeld surface analysis and 2D fingerprint plotting. Reciprocal H…H contacts contributed most (52.9 %) to the Hirshfeld surface, followed by C…H/H…C contacts (30.2 %), whereas, O…H/H…O and N…H/H…N interactions contributed 15.5 % to the Hirshfeld surface. Electrostatic potentials were mapped over the Hirshfeld surface to analyze electrostatic complementarities within the MBA-dMPP crystal. In addition, geometrical descriptors were also analyzed to the extent of surface interactions. MBA-dMPP was also investigated for in vitro antibacterial activity against Gram-positive and Gram-negative bacterial strains, and showed highest activity against Bacillus cereus (MIC = 12.5 μg mL-1) and Salmonellatythimurium (MIC = 50 μg mL-1). In silico screening was conducted by docking MBA-dMPP on the active site of S12 bacterial protein (an important therapeutic target of antibacterial agents) and its binding properties were compared with those of ciprofloxacin. Moreover, a field points map of MBA-dMPP ligand was studied to determine electrostatic and van der Waals forces, hydrophobic potentials, and positions involved in ligand-receptor interactions. Finally, the torsion energies of crystal structure and optimized and bioactive conformers of MBA-dMPP were compared to predict its bioactive conformation.

Dataset Information

Synthesis, crystal structure and antibacterial studies of dihydropyrimidines and their regioselectively oxidized products.

Publications

Synthesis, crystal structure and antibacterial studies of dihydropyrimidines and their regioselectively oxidized products.

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