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Molecules 2012, 17(10), 12072-12085; doi:10.3390/molecules171012072
Article

A Novel Class of Selective Acetylcholinesterase Inhibitors: Synthesis and Evaluation of (E)-2-(Benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles

1,2, 1, 2, 3, 2, 1,*  and 4,*
Received: 23 July 2012; in revised form: 30 August 2012 / Accepted: 17 September 2012 / Published: 15 October 2012
(This article belongs to the Section Medicinal Chemistry)
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Abstract: (E)-2-(benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles are described as a new class of selective inhibitors of acetylcholinesterase (AChE). The most potent compound in the series exhibited good AChE inhibitory activity (IC50 = 64 µM). Compound 7f was found to be more selective than galanthamine in inhibiting AChE and it showed a moderate selectivity index. Kinetic studies on AChE indicated that a competitive type of inhibition pattern exist for these acrylonitrile derivates. Molecular docking models of the ligand-AChE complexes suggest that compound 7g is located on the periphery of the AChE active site.
Keywords: Knoevenagel condensation; acrylonitriles; AChE inhibitors; docking; ligand-protein interactions; selectivity Knoevenagel condensation; acrylonitriles; AChE inhibitors; docking; ligand-protein interactions; selectivity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Torre, P.; Saavedra, L.A.; Caballero, J.; Quiroga, J.; Alzate-Morales, J.H.; Cabrera, M.G.; Trilleras, J. A Novel Class of Selective Acetylcholinesterase Inhibitors: Synthesis and Evaluation of (E)-2-(Benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles. Molecules 2012, 17, 12072-12085.

AMA Style

Torre P, Saavedra LA, Caballero J, Quiroga J, Alzate-Morales JH, Cabrera MG, Trilleras J. A Novel Class of Selective Acetylcholinesterase Inhibitors: Synthesis and Evaluation of (E)-2-(Benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles. Molecules. 2012; 17(10):12072-12085.

Chicago/Turabian Style

Torre, Pedro ; Saavedra, Luis A.; Caballero, Julio; Quiroga, Jairo; Alzate-Morales, Jans H.; Cabrera, Margarita G.; Trilleras, Jorge. 2012. "A Novel Class of Selective Acetylcholinesterase Inhibitors: Synthesis and Evaluation of (E)-2-(Benzo[d]thiazol-2-yl)-3-heteroarylacrylonitriles." Molecules 17, no. 10: 12072-12085.


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