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

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Author(s): Yorley Duarte | Margarita Gutiérrez | Luis Astudillo | Jans Alzate-Morales | Natalia Valdés

Journal: Molecules
ISSN 1420-3049

Volume: 18;
Issue: 10;
Start page: 12951;
Date: 2013;
Original page

Keywords: bistetrahydroquinolines | Diels-Alder reaction | AChE and BuChE inhibitors | molecular docking | MM-GBSA

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.
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Tango Jona
Tangokurs Rapperswil-Jona