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Synthesis, characterization, biological evaluation, and in silico studies of novel 1,3‐diaryltriazene‐substituted sulfathiazole derivatives
Author(s) -
Işık Mesut,
Akocak Süleyman,
Lolak Nabih,
Taslimi Parham,
Türkeş Cüneyt,
Gülçin İlhami,
Durgun Mustafa,
Beydemir Şükrü
Publication year - 2020
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.202000102
Subject(s) - chemistry , thiadiazoles , carbonic anhydrase , stereochemistry , carbonic anhydrase i , proton nmr , sulfathiazole , enzyme , aché , nuclear magnetic resonance spectroscopy , chemical synthesis , carbon 13 nmr , molecule , acetylcholinesterase , nuclear chemistry , medicinal chemistry , in vitro , organic chemistry , biochemistry
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.