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