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Molecules 2013, 18(10), 12951-12965; doi:10.3390/molecules181012951

Synthesis of Bistetrahydroquinolines as Potential Anticholinesterasic Agents by Double Diels-Alder Reactions

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
*
Author to whom correspondence should be addressed.
Received: 2 September 2013 / Revised: 27 September 2013 / Accepted: 8 October 2013 / Published: 17 October 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

The tetrahydroquinoline ring system is a unit found in many biologically active natural products and pharmacologically relevant therapeutic agents. A new series of bistetrahydroquinolines (bis-THQs) was synthesized using imino Diels-Alder reactions between dialdehydes, anilines and N-vinyl-2-pyrrolidone (NVP). The notable features of this procedure are mild reaction conditions, greater selectivity and good yields of products. In addition, the inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) of some selected derivatives is reported. The feasible binding modes of these active compounds, within AChE and BuChE binding sites, were predicted by molecular docking experiments and their binding affinity was estimated by means of free energy calculations through the MM-GBSA approximation.
Keywords: bistetrahydroquinolines; Diels-Alder reaction; AChE and BuChE inhibitors; molecular docking; MM-GBSA bistetrahydroquinolines; Diels-Alder reaction; AChE and BuChE inhibitors; molecular docking; MM-GBSA
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Duarte, Y.; Gutiérrez, M.; Astudillo, L.; Alzate-Morales, J.; Valdés, N. Synthesis of Bistetrahydroquinolines as Potential Anticholinesterasic Agents by Double Diels-Alder Reactions. Molecules 2013, 18, 12951-12965.

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