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

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Huseynzada A., Mori M., Meneghetti F., Israyilova A., Guney E., SAYIN K., ...Daha Fazla

Crystals, cilt.13, sa.1, 2023 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 13 Sayı: 1
  • Basım Tarihi: 2023
  • Doi Numarası: 10.3390/cryst13010052
  • Dergi Adı: Crystals
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aerospace Database, Applied Science & Technology Source, Chemical Abstracts Core, Communication Abstracts, Computer & Applied Sciences, INSPEC, Metadex, Directory of Open Access Journals, Civil Engineering Abstracts
  • Anahtar Kelimeler: 1, 2-dihydropyrimidines, regioselective oxidation, intramolecular hydrogen bonds, Hirshfeld surface analysis, molecular docking, antimycotic activity
  • Sivas Cumhuriyet Üniversitesi Adresli: Evet

Özet

© 2022 by the authors.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.