Synthesis, characterization, biological evaluation, and in silico studies of novel 1,3-diaryltriazene-substituted sulfathiazole derivatives

IŞIK M., AKOCAK S., Lolak N., Taslimi P., TÜRKEŞ C., GÜLÇİN İ., ...Daha Fazla

ARCHIV DER PHARMAZIE, cilt.353, sa.9, 2020 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 353 Sayı: 9
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1002/ardp.202000102
  • Dergi Adı: ARCHIV DER PHARMAZIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, BIOSIS, CAB Abstracts, Chimica, EMBASE, International Pharmaceutical Abstracts, MEDLINE, Veterinary Science Database, Index Chemicus (IC)
  • Anahtar Kelimeler: enzyme inhibition, metabolic enzymes, molecular docking, sulfathiazole, triazene, CARBONIC-ANHYDRASE I, CRYSTAL-STRUCTURE, INHIBITORY PROPERTIES, MOLECULAR-DOCKING, ACETYLCHOLINESTERASE, SULFONAMIDES, POTENT, VITRO, DESIGN, BUTYRYLCHOLINESTERASE
  • Anadolu Üniversitesi Adresli: Evet

Özet

In the present study, a series of eleven novel 1,3-diaryltriazene-substituted sulfathiazole moieties (ST1-11) was synthesized by the reaction of diazonium salt of sulfathiazole with substituted aromatic amines and their chemical structures were characterized by Fourier transform infrared,H-1-NMR (nuclear magnetic resonance),C-13-NMR, and high-resolution mass spectroscopy methods. These synthesized novel derivatives were found to be effective inhibitor molecules for alpha-glycosidase (alpha-GLY), human carbonic anhydrase (hCA), and acetylcholinesterase (AChE), withK(I)values in the range of 426.84 +/- 58.42-708.61 +/- 122.67 nM for alpha-GLY, 450.37 +/- 50.35-1,094.34 +/- 111.37 nM forhCA I, 504.37 +/- 57.22-1,205.36 +/- 195.47 nM forhCA II, and 68.28 +/- 10.26-193.74 +/- 19.75 nM for AChE. Among the synthesized novel compounds, several lead compounds were investigated against the tested metabolic enzymes. More specifically,ST11(4-[3-(perfluorophenyl)triaz-1-en-1-yl]-N-(thiazol-2-yl)benzenesulfonamide) showed a highly efficient inhibition profile againsthCA I,hCA II, and AChE, withK(I)values of 450.37 +/- 50.35, 504.37 +/- 57.22, and 68.28 +/- 10.26 nM, respectively. Due to its significant biological inhibitory potency, this derivative may be considered as an interesting lead compound against these enzymes.