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

Mamedova, Gulnar; Mahmudova, Adila; Mamedov, Sabir; ERDEN, YAVUZ; Taslimi, Parham; TÜZÜN, BURAK; TAŞ, RECEP; Farzaliyev, Vagif; Sujayev, Afsun; Alwasel, Saleh H.; Gülçin, İlhami

doi:10.1016/j.bioorg.2019.103313

Makale Tam Makale Uluslararası 2019

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

Gulnar Mamedova, Adila Mahmudova, Sabir Mamedov, YAVUZ ERDEN, Parham Taslimi, BURAK TÜZÜN, RECEP TAŞ, Vagif Farzaliyev, Afsun Sujayev, Saleh H. Alwasel, İlhami Gülçin

Bioorganic Chemistry Cilt 93 · 01.12.2019

DOI ile aç

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.

Anahtar kelimeler

antioxidant DERIVATIVES Acetylcholinesterase Butyrylcholinesterase Molecular docking enzyme inhibition anticancer CHOLINESTERASE BIOLOGICAL EVALUATION CRYSTAL-STRUCTURE Pyrazole POTENT CARBONIC-ANHYDRASE INHIBITION alpha-glycosidase POLYPHENOL CONTENTS sulfamide

Atıf için künye

Mamedova, G., Mahmudova, A., Mamedov, S., ERDEN, Y., Taslimi, P., TÜZÜN, B., TAŞ, R., Farzaliyev, V., Sujayev, A., Alwasel, S. H., & Gülçin, İ. (2019). Novel tribenzylaminobenzolsulphonylimine based on their pyrazine and pyridazines: Synthesis, characterization, antidiabetic, anticancer, anticholinergic, and molecular docking studies. Bioorganic Chemistry, 93. https://doi.org/10.1016/j.bioorg.2019.103313

BibTeX

@article{mamedova2019-68020,
  author = {Mamedova, Gulnar and Mahmudova, Adila and Mamedov, Sabir and ERDEN, YAVUZ and Taslimi, Parham and TÜZÜN, BURAK and TAŞ, RECEP and Farzaliyev, Vagif and Sujayev, Afsun and Alwasel, Saleh H. and Gülçin, İlhami},
  title = {Novel tribenzylaminobenzolsulphonylimine based on their pyrazine and pyridazines: Synthesis, characterization, antidiabetic, anticancer, anticholinergic, and molecular docking studies},
  journal = {Bioorganic Chemistry},
  year = {2019},
  volume = {93},
  issn = {0045-2068},
  doi = {10.1016/j.bioorg.2019.103313},
  url = {https://akademik.atauni.edu.tr/yayinlar/68020-novel-tribenzylaminobenzolsulphonylimine-based-on-their-pyrazine-and-pyridazines}
}