(2015) 9H-Carbazole Derivatives Containing the N-Benzyl-1,2,3-triazole Moiety as New Acetylcholinesterase Inhibitors. Archiv der Pharmazie. pp. 366-374.
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Abstract
A series of triazole-containing carbazole derivatives were designed as new anti-acetylcholinesterase (AChE) agents. The target compounds 6a-q were simply prepared via a one-pot three-component click reaction of N-propargyl-9H-carbazole, sodium azide, and an appropriate benzyl halide. The in vitro anti-cholinesterase assay showed that the unsubstituted benzyl derivative 6p along with the 2-F, 2-Me, 3-Me, 3-MeO, and 3-F analogs (6a, 6c, and 6g-i) had significant anti-AChE activity (IC<inf>50</inf>s�3.8μM). Among them, the 2-methylbenzyl derivative 6c with an IC<inf>50</inf> value of 1.9μM was the most active compound. The SAR studies revealed that small halogen atoms such as the fluorine atom or electron-donating groups such as methyl or methoxy at the ortho or meta positions of the benzyl pendent group could be tolerated or improved the anti-AChE activity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
| Item Type: | Article |
|---|---|
| Keywords: | 1,2,3 triazole derivative; 9 (1 benzyl 1h 1,2,3 triazol 4 yl)methyl 9h carbazole; 9 1 (2 chloro 6 fluorobenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (2 chlorobenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (2 fluorobenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (2 methylbenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (2 nitrobenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (2,4 dichlorobenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (3 chlorobenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (3 fluorobenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (3 methoxybenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (3 methylbenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (4 bromobenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (4 chlorobenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (4 fluorobenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (4 methoxybenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (4 methylbenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; 9 1 (4 nitrobenzyl) 1h 1,2,3 triazol 4 yl]methyl] 9h carbazole; acetylcholinesterase; benzyl derivative; carbazole derivative; cholinesterase inhibitor; halide; halogen; sodium azide; unclassified drug; acetylcholinesterase; carbazole derivative; cholinesterase inhibitor; ligand; protein binding; triazole derivative, Article; atom; cholinesterase inhibition; click chemistry; drug design; electron; enzyme kinetics; IC50; in vitro study; molecular docking; nonhuman; priority journal; structure activity relation; binding site; chemical structure; comparative study; kinetics; metabolism; synthesis, Acetylcholinesterase; Binding Sites; Carbazoles; Cholinesterase Inhibitors; Drug Design; Kinetics; Ligands; Molecular Docking Simulation; Molecular Structure; Protein Binding; Structure-Activity Relationship; Triazoles |
| Page Range: | pp. 366-374 |
| Journal or Publication Title: | Archiv der Pharmazie |
| Volume: | 348 |
| Number: | 5 |
| Publisher: | Wiley-VCH Verlag |
| Depositing User: | ms soheila Bazm |
| URI: | http://eprints.ssu.ac.ir/id/eprint/9234 |
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