Novel tribenzylaminobenzolsulphonylimine based on their pyrazine and pyridazines: Synthesis, characterization, antidiabetic, anticancer, anticholinergic, and molecular docking studies

Mamedova G., Mahmudova A., Mamedov S., ERDEN Y., Taslimi P., TÜZÜN B., ...Daha Fazla

BIOORGANIC CHEMISTRY, cilt.93, 2019 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 93
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.bioorg.2019.103313
  • Dergi Adı: BIOORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Anahtar Kelimeler: Pyrazole, Sulfamide, Anticancer, Enzyme inhibition, Molecular docking, Cholinesterase, CARBONIC-ANHYDRASE INHIBITION, CRYSTAL-STRUCTURE, ALPHA-GLYCOSIDASE, BIOLOGICAL EVALUATION, POLYPHENOL CONTENTS, DERIVATIVES, ACETYLCHOLINESTERASE, ANTIOXIDANT, BUTYRYLCHOLINESTERASE, POTENT
  • Atatürk Üniversitesi Adresli: Evet

Özet

A new method of obtaining multifunctional pyrazoles by the reaction of 1,3-dipolar addition of tribenzylsulfonyliminochloride to polarophiles has been developed. This imine is obtained by reacting tribenzylamine with N-chlorobenzene sulfamide (chloramine-B). Regardless of the structure and composition of polarophiles, the cyclization reaction takes place in the presence of alkali in 6-8 h of boiling, which proves the activation of the methylene groups of tribenzylamine using the electron-withdrawing sulfonamide group. These novel derivatives were effective inhibitors of the alpha-glycosidase, butyrylcholinesterase (BChE), and alpha-cetylcholinesterase enzymes (AChE) with Ki values in the range of 0.45 +/- 0.08-1.24 +/- 0.27 mu M for alpha-glycosidase, 6.04 +/- 0.95-11.61 +/- 2.84 mu M for BChE, and 2.04 +/- 0.24-4.23 +/- 1.02 mu M for AChE, respectively. The biological activities of the studied molecules against enzyme molecules were investigated by molecular docking calculations. The enzymes studied were AChE for ID 4M0E, BChE for ID 5NN0 BChE, and alpha-Glycosidase for ID 1XSI (alpha-Gly) respectively.