Synthesis, characterization, biological evaluation, and in silico studies of novel 1,3‐diaryltriazene‐substituted sulfathiazole derivatives
Mesut Işık, Süleyman Akocak, Nebih Lolak, Parham Taslımı, Cüneyt Türkeş, İlhami Gülçın, Mustafa Durgun, Şükrü Beydemir
Abstract
Abstract 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, 1 H‐NMR (nuclear magnetic resonance), 13 C‐NMR, and high‐resolution mass spectroscopy methods. These synthesized novel derivatives were found to be effective inhibitor molecules for α‐glycosidase (α‐GLY), human carbonic anhydrase ( h CA), and acetylcholinesterase (AChE), with K I values in the range of 426.84 ± 58.42–708.61 ± 122.67 nM for α‐GLY, 450.37 ± 50.35–1,094.34 ± 111.37 nM for h CA I, 504.37 ± 57.22–1,205.36 ± 195.47 nM for h CA 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 against h CA I, h CA II, and AChE, with K 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.