Crystal Structure, Hirshfeld Surface Analysis, In-Silico and Antimycotic Investigations of Methyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyrimidine-5-carboxylate

Herein, we report the preparation of methyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyrimidine-5-carboxylate 2, obtained by the regioselective oxidative dehydrogenation of the dihydropyrimidine derivative 1 in the presence of cerium ammonium nitrate. The structure of compound 2 was investigated...

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Published in:Crystals (Basel) 2023-01, Vol.13 (1), p.52
Main Authors: Huseynzada, Alakbar, Mori, Matteo, Meneghetti, Fiorella, Israyilova, Aygun, Guney, Elif, Sayin, Koray, Chiarelli, Laurent R., Demiralp, Mustafa, Hasanova, Ulviyya, Abbasov, Vagif
Format: Article
Language:English
Subjects:
1,2-dihydropyrimidines
Ammonium nitrate
antimycotic activity
Biological activity
Cerium ammonium nitrate
Chromatography
Crystal structure
Dehydrogenation
Hirshfeld surface analysis
intramolecular hydrogen bonds
molecular docking
regioselective oxidation
Single crystals
Surface analysis (chemical)
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Summary:Herein, we report the preparation of methyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyrimidine-5-carboxylate 2, obtained by the regioselective oxidative dehydrogenation of the dihydropyrimidine derivative 1 in the presence of cerium ammonium nitrate. The structure of compound 2 was investigated by single-crystal X-ray diffraction (SC-XRD), which allowed the determination of its tautomeric form. Moreover, the presence of non-covalent interactions and their impact on the crystal structure were analyzed. To better characterize the intermolecular contacts, the Hirshfeld surface and enrichment ratio analyses were performed. Furthermore, the antimycotic activity of compounds 1 and 2 was investigated against Candida albicans, Aspergillus flavus, and Aspergillus niger, and their efficacy was compared to that of fluconazole. Computational investigations on the putative target of the compounds provided insights to explain the better activity of 2 with respect to its synthetic precursor.
ISSN:2073-4352
2073-4352
DOI:10.3390/cryst13010052