Synthesis, DFT calculations, spectroscopy and in vitro antioxidant activity studies on 4-hydroxyphenyl substituted thiopyrimidine derivatives

Akbaş E., Ekin S., Ergan E., Karakuş Y.

Journal of Molecular Structure, vol.1174, pp.177-183, 2018 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1174
  • Publication Date: 2018
  • Doi Number: 10.1016/j.molstruc.2018.02.080
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.177-183
  • Keywords: Synthesis, Thiopyrimidines, DFT calculations, Antioxidant activity, DENSITY, INHIBITORS, CORROSION, AGENTS


© 2018 Elsevier B.V.4-Hydroxyphenyl substituted thiopyrimidine derivatives have been synthesized with the starting compound 5-benzoyl-6-phenyl-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydro-2-thioxopyrimidine (1). The compounds optimized geometrically with DFT in Gaussian at the B3LYP/6-31G (d, p) level in order to obtain information about the 3D geometries and electronic structures. The structures were characterized on the basis of 1H NMR, 13C NMR, FT-IR, and elemental analysis. All compounds tested in vitro in order to assess their antioxidant activity. On the biological properties including of free radical scavenging ability (DPPH•), ABTS•+ assay, PhNHNH2 (phenyl hydrazine) induced haemolysis of erythrocytes and metal chelating activities were performed. The results were compared to standard antioxidants, such as α-tocopherol and trolox. The conclusion shows that the compounds thioxopyrimidine (1), dihydropyrimido[2,1-b][1,3]thiazin-4(6H)-one (4) and dihydropyrimidin-2(1H)-ylidene) malonate (5) exhibit a stronger antioxidant activity than the other derivatives.