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

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 di...

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Bibliographic Details
Published in:RSC advances 2021-02, Vol.11 (11), p.6312-6329
Main Authors: Huseynzada, Alakbar E, Jelch, Christian, Akhundzada, Haji Vahid N, Soudani, Sarra, Ben Nasr, Cherif, Israyilova, Aygun, Doria, Filippo, Hasanova, Ulviyya A, Khankishiyeva, Rana F, Freccero, Mauro
Format: Article
Language:English
Subjects:
Ammonium nitrate
Antiinfectives and antibacterials
Bacteria
Cerium ammonium nitrate
Chemical Sciences
Chemistry
Copper
Cristallography
Crystal structure
Crystallography
Derivatives
E coli
Hydrogen bonds
Investigations
Klebsiella
Oxidation
Pseudomonas aeruginosa
Regioselectivity
Single crystals
Tautomers
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Summary: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. Known methods of synthesis of dihydropyrimidines and their oxidized products were modified, the impact of hydrogen bonds on stabilization of preferred tautomer and biological activities were studied.
ISSN:2046-2069
2046-2069
DOI:10.1039/d0ra10255e