Crystal Structure, Hirshfeld Surface Analysis, In-Silico and Antimycotic Investigations of Methyl 6-methyl-4-(4-nitrophenyl)-2-oxo-1,2-dihydropyrimidine-5-carboxylate
Creators
- 1. Univ Milan, Dept Pharmaceut Sci, Via L Mangiagalli 25, I-20133 Milan, Italy
- 2. Sivas Cumhuriyet Univ, Fac Sci, Chem Dept, TR-58140 Sivas, Turkiye
- 3. Univ Pavia, Dept Biol & Biotechnol, Via A Ferrata 9, I-27100 Pavia, Italy
- 4. Sivas Cumhuriyet Univ, Adv Technol Res & Applicat Ctr, TR-58140 Sivas, Turkiye
- 5. Inst Petrochem Proc, K Ave 30, AZ-1005 Baku, Azerbaijan
Description
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.
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