2026-10-18T23:14:55Zhttps://ebyu-rdlopen.rawdatalibrary.net/oai/request

oai:ebyu-rdlopen.rawdatalibrary.net:ebyu/135962026-10-18T21:13:28Zopenairedrivercom_ebyu_10000col_ebyu_10001

Synthesis, characterization, biological evaluation, and in silico studies of novel 1,3-diaryltriazene-substituted sulfathiazole derivativesIşık, MesutAkocak, SüleymanLolak, NabihTaslimi, ParhamTürkeş, CüneytGülçin, İlhamiDurgun, MustafaBeydemir, Şükrüenzyme inhibitionmetabolic enzymesmolecular dockingsulfathiazoletriazeneCaco-2 CellsCarbonic Anhydrase InhibitorsCholinesterase InhibitorsComputer SimulationGlycoside Hydrolase InhibitorsHumansMagnetic Resonance SpectroscopyMass SpectrometrySpectroscopy, Fourier Transform InfraredStructure-Activity RelationshipSulfathiazolesTriazenes4 (3 phenyltriaz 1 en 1 yl) n (thiazol 2 yl)benzenesulfonamide4 [3 (3 nitrophenyl)triaz 1 en 1 yl] n (thiazol 2 yl)benzenesulfonamide4 [3 (3,4 dichlorophenyl)triaz 1 en 1 yl] n (thiazol 2 yl)benzenesulfonamide4 [3 (3,4 dimethoxyphenyl)triaz 1 en 1 yl] n (thiazol 2 yl)benzenesulfonamide4 [3 (3,5 dimethylphenyl)triaz 1 en 1 yl] n (thiazol 2 yl)benzenesulfonamide4 [3 (4 acetylphenyl)triaz 1 en 1 yl] n (thiazol 2 yl)benzenesulfonamide4 [3 (4 chlorophenyl)triaz 1 en 1 yl] n (thiazol 2 yl)benzenesulfonamide4 [3 (4 fluorophenyl)triaz 1 en 1 yl] n (thiazol 2 yl)benzenesulfonamide4 [3 (4 methoxyphenyl)triaz 1 en 1 yl] n (thiazol 2 yl)benzenesulfonamide4 [3 (perfluorophenyl)triaz 1 en 1 yl] n (thiazol 2 yl)benzenesulfonamide4 [3 [4 [n (thiazol 2 yl)sulfamoyl]phenyl]triaz 2 en 1 yl]benzoic acidacarboseacetazolamideIn 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, 1H-NMR (nuclear magnetic resonance), 13C-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 (hCA), and acetylcholinesterase (AChE), with KI 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 hCA I, 504.37 ± 57.22–1,205.36 ± 195.47 nM for hCA 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 hCA I, hCA II, and AChE, with KI 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. © 2020 Deutsche Pharmazeutische GesellschaftWiley-VCH Verlag2020Articlehttps://rdlopen.rawdatalibrary.net/r/ebyu/13596https://doi.org/10.1002/ardp.2020001020365-6233enArchiv der Pharmazieinfo:eu-repo/semantics/openAccessinfo:eu-repo/semantics/articlehttps://ebyu-rdlopen.rawdatalibrary.net/tr/items/ebyu/13596