Next Article in Journal
c-IAP1 Binds and Processes PCSK9 Protein: Linking the c-IAP1 in a TNF-α Pathway to PCSK9-Mediated LDLR Degradation Pathway
Previous Article in Journal
Synthesis and Photophysical Study of 2′-Deoxyuridines Labeled with Fluorene Derivatives
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,*
1 Laboratorio Síntesis Orgánica, Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, 3460000, Chile 2 Centro de Bioinformática y Simulación Molecular, Universidad de Talca, 2 Norte 685, Casilla 721, Talca, 3460000, Chile 3 Grupo de Investigación de Compuestos Heterocíclicos, Department of Chemistry, Universidad del Valle A. A. 25360 Cali, Colombia 4 Grupo de Investigación en Compuestos Heterocíclicos, Programa de Química, Facultad de Ciencias Básicas, Universidad del Atlántico, Km 7 Antigua vía Puerto Colombia, A.A.1890, Barranquilla, Colombia
* Authors to whom correspondence should be addressed.
Received: 23 July 2012 / Revised: 30 August 2012 / Accepted: 17 September 2012 / Published: 15 October 2012
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [328 KB, uploaded 18 June 2014]   |   Browse Figures
SciFeed

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 (CC BY 3.0).

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert