Selenourea and thiourea derivatives of chiral and achiral enetetramines: Synthesis, characterization and enzyme inhibitory properties

YİĞİT M., BARUT CELEPCİ D., Taslimi P., YİĞİT B., Cetinkaya E., ÖZDEMİR İ., ...Daha Fazla

BIOORGANIC CHEMISTRY, cilt.120, 2022 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 120
  • Basım Tarihi: 2022
  • Doi Numarası: 10.1016/j.bioorg.2021.105566
  • Dergi Adı: BIOORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Chimica, EMBASE, MEDLINE, Veterinary Science Database
  • Anahtar Kelimeler: Chiral selenourea, Thiourea, Enetetramine, Crystal structure, Enzyme inhibition, Achethylcholinesterase, Butyrylcholinesterase, N-HETEROCYCLIC CARBENE, ALPHA-GLUCOSIDASE INHIBITORS, ELECTRON-RICH OLEFINS, CARBONIC-ANHYDRASE, CRYSTAL-STRUCTURE, BENZIMIDAZOLE DERIVATIVES, VIBRATIONAL PROPERTIES, BIOLOGICAL EVALUATION, METAL-COMPLEXES, IN-VITRO
  • İnönü Üniversitesi Adresli: Evet

Özet

A series of chiral and achiral cyclic seleno-and thiourea compounds bearing benzyl groups on N-atoms were prepared from enetetramines and appropriate Group VI elements in good yields. All the synthesized compounds were characterized by elemental analysis, FT-IR, H-1 NMR and C-13 NMR spectroscopy, and the molecular and crystal structures of (R,R)-4b and (R,R)-5b were confirmed by the single-crystal X-ray diffraction method. These assayed for their activities against metabolic enzymes acetylcholinesterase, butyrylcholinesterase, and alpha-glycosidase. These selenourea and thiourea derivatives of chiral and achiral enetetramines effectively inhibit AChE and BChE with IC50 values in the range of 3.32-11.36 and 1.47-9.73 mu M, respectively. Also, these compounds inhibited alpha-glycosidase enzyme with IC50 values varying between 1.37 and 8.53 mu M. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against alpha-glycosidase enzyme, (S,S)-5b, was 12-times more potent than standard inhibitor acarbose; 7b and 8a as most potent compounds against cholinesterase enzymes, were around 5 and 13-times more potent than standard inhibitor tacrine against achethylcholinesterase (AChE) and butyrylcholinesterase (BChE), respectively.