Saeedi, M. and Rastegari, A. and Hariri, R. and Mirfazli, S.S. and Mahdavi, M. and Edraki, N. and Firuzi, O. and Akbarzadeh, T. (2020) Design and Synthesis of Novel Arylisoxazole-Chromenone Carboxamides: Investigation of Biological Activities Associated with Alzheimer's Disease. Chemistry and Biodiversity, 17 (5).
Full text not available from this repository.Abstract
A novel series of hybrid arylisoxazole-chromenone carboxamides were designed, synthesized, and evaluated for their cholinesterase (ChE) inhibitory activity based on the modified Ellman's method. Among synthesized compounds, 5-(3-nitrophenyl)-N-4-(2-oxo-2H-1-benzopyran-7-yl)oxyphenyl-1,2-oxazole-3-carboxamide depicted the most acetylcholinesterase (AChE) inhibitory activity (IC50=1.23 μm) and 5-(3-chlorophenyl)-N-4-(2-oxo-2H-1-benzopyran-7-yl)oxyphenyl-1,2-oxazole-3-carboxamide was found to be the most potent butyrylcholinesterase (BChE) inhibitor (IC50=9.71 μm). 5-(3-Nitrophenyl)-N-4-(2-oxo-2H-1-benzopyran-7-yl)oxyphenyl-1,2-oxazole-3-carboxamide was further investigated for its BACE1 inhibitory activity as well as neuroprotectivity and metal chelating ability as important factors involved in onset and progress of Alzheimer's disease. It could inhibit BACE1 by 48.46 at 50 μm. It also showed 6.4 protection at 25 μm and satisfactory chelating ability toward Zn2+, Fe2+, and Cu2+ ions. Docking studies of 5-(3-nitrophenyl)-N-4-(2-oxo-2H-1-benzopyran-7-yl)oxyphenyl-1,2-oxazole-3-carboxamide and 5-(3-chlorophenyl)-N-4-(2-oxo-2H-1-benzopyran-7-yl)oxyphenyl-1,2-oxazole-3-carboxamide confirmed desired interactions with those amino acid residues of the AChE and BChE, respectively. © 2020 Wiley-VHCA AG, Zurich, Switzerland
| Item Type: | Article |
|---|---|
| Additional Information: | cited By 1 |
| Uncontrolled Keywords: | 5 (2 chlorophenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; 5 (2 fluorophenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; 5 (3 chlorophenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; 5 (3 methoxyphenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; 5 (3 nitrophenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; 5 (3,4 dimethoxyphenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; 5 (4 bromophenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; 5 (4 chlorophenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; 5 (4 fluorophenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; 5 (4 methoxyphenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; 5 (4 methylphenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; 5 (4 nitrophenyl) n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 1,2 oxazole 3 carboxamide; acetylcholinesterase; amide; amyloid beta protein25-35; amyloid protein; beta secretase 1; cholinesterase; cholinesterase inhibitor; chromene derivative; cupric ion; donepezil; n 4 (2 oxo 2h 1 benzopyran 7 yl)oxy]phenyl] 5 phenyl 1,2 oxazole 3 carboxamide; oxazole derivative; unclassified drug, Alzheimer disease; Article; biological activity; cell viability; chelation; cholinesterase inhibition; competitive inhibition; controlled study; drug conformation; drug design; drug potency; drug synthesis; enzyme active site; hydrogen bond; hydrophobicity; IC50; metal binding; molecular docking; neuroprotection; PC12 cell line (pheochromocytoma); stoichiometry |
| Subjects: | WL Nervous System |
| Depositing User: | eprints admin |
| Date Deposited: | 14 Sep 2020 03:50 |
| Last Modified: | 14 Sep 2020 03:50 |
| URI: | http://eprints.iums.ac.ir/id/eprint/23689 |
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