Synthesis, characterization, antioxidant, antidiabetic, anticholinergic, and antiepileptic properties of novel N-substituted tetrahydropyrimidines based on phenylthiourea

MAHARRAMOVA G., TASLIMI P., Sujayev A., Farzaliyev V., DURMAZ L., GÜLÇİN İ.

JOURNAL OF BIOCHEMICAL AND MOLECULAR TOXICOLOGY, cilt.32, sa.12, 2018 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 32 Sayı: 12
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1002/jbt.22221
  • Dergi Adı: JOURNAL OF BIOCHEMICAL AND MOLECULAR TOXICOLOGY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Anahtar Kelimeler: acetylcholinesterase, antioxidant activity, butyrylcholinesterase, carbonic anhydrase, phenylthiourea, CARBONIC-ANHYDRASE, ALPHA-GLUCOSIDASE, INHIBITION PROFILES, POLYPHENOL CONTENT, PHASE SYNTHESIS, SOLID-PHASE, ACETYLCHOLINESTERASE, BUTYRYLCHOLINESTERASE, DERIVATIVES, BROMOPHENOLS
  • Atatürk Üniversitesi Adresli: Evet

Özet

In the presence of trifluoroacetic acid, on the basis of three-component condensation of phenylthiourea with its salicylaldehyde and methyl-3-oxobutanoate, an efficient method for the synthesis of 1-(4-(2-hydroxyphenyl)-6-methyl-1-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethanone (I) has been worked out. These novel N-substituted tetrahydropyrimidines based on phenylthiourea showed good inhibitory action against acetylcholinesterase (AChE), alpha-glycosidase, and human carbonic anhydrase (hCA) isoforms I and II. K-i values of AChE enzyme were in the range of 0.48 to 7.46 nM. The hCA I and II were effectively inhibited by the compounds, with K-i values in the range of 502.44 to 923.11 nM for hCA I and 400.32 to 801.57 nM for hCA II, respectively. The antioxidant activity of the novel N-substituted tetrahydropyrimidines based on phenylthiourea was investigated by using different in vitro antioxidant assays; including 1,1-diphenyl-2-picrylhydrazyl (DPPH center dot) radical scavenging, Cu2+ and Fe3+ reducing activities.