(2016) Synthesis and anticholinesterase activity of coumarin-3-carboxamides bearing tryptamine moiety. European Journal of Medicinal Chemistry. pp. 40-46.
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Abstract
A number of N-(2-(1H-indol-3-yl)ethyl)-2-oxo-2H-chromene-3-carboxamides were synthesized and tested against AChE and BuChE. The in vitro assessment of the synthesized compounds 4a-o revealed that most of them had significant activity toward AChE. The SAR study demonstrated that the introduction of benzyloxy moiety on the 7-position of coumarin scaffold can improve the anti-AChE activity. The best result was obtained with 7-(4-fluorobenzyl)oxy moiety in the case of compound 4o, displaying IC50value of 0.16 μM. Based on the docking study of AChE, the prototype compound 4o was laid across the active site and occupied both peripheral anionic site (PAS) and catalytic anionic site (CAS). © 2016 Elsevier Masson SAS
| Item Type: | Article |
|---|---|
| Keywords: | 6 bromo n 2 (1h indol 3 yl)ethyl 2 oxo chromene 3 carboxamide; acetylcholinesterase; amide; cholinesterase; chromene derivative; coumarin derivative; n 2 (1h indol 3 yl)ethyl 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 2 oxo 7 propoxy 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 7 (2 fluorobenzyloxy) 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 7 (2,3 dichlorobenzyloxy) 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 7 (3,4 dichlorobenzyloxy) 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 7 (4 chlorobenzyloxy) 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 7 (benzyloxy) 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 7 ethoxy 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 7 hydroxy 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 7 methoxy 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 7 (2 chlorobenzyl)oxy 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 7 (3 fluorobenzyl)oxy 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 7 (4 fluorobenzyl)oxy 2 oxo 2h chromene 3 carboxamide; n 2 (1h indol 3 yl)ethyl 8 methoxy 2 oxo 2h chromene 3 carboxamide; unclassified drug; acetylcholinesterase; cholinesterase; cholinesterase inhibitor; coumarin derivative; tryptamine; tryptamine derivative, Article; cholinesterase inhibition; crystal structure; cyclization; drug synthesis; enzyme active site; enzyme kinetics; IC50; in vitro study; microwave irradiation; molecular docking; structure activity relation; animal; chemistry; drug effects; human; synthesis, Acetylcholinesterase; Animals; Butyrylcholinesterase; Catalytic Domain; Cholinesterase Inhibitors; Coumarins; Humans; Molecular Docking Simulation; Structure-Activity Relationship; Tryptamines |
| Page Range: | pp. 40-46 |
| Journal or Publication Title: | European Journal of Medicinal Chemistry |
| Volume: | 121 |
| Publisher: | Elsevier Masson SAS |
| Depositing User: | ms soheila Bazm |
| URI: | http://eprints.ssu.ac.ir/id/eprint/9755 |
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