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

Molecules

Yorley Duarte¹  Margarita Gutiérrez¹  Luis Astudillo¹  Jans Alzate-Morales² 

[1] Laboratorio Síntesis Orgánica, Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca 3460000, Chile; E-Mails:;Centro de Bioinformática y Simulación Molecular, Universidad de Talca, 2 Norte 685, Casilla 721, Talca 3460000, Chile; E-Mails:

关键词: bistetrahydroquinolines;    Diels-Alder reaction;    AChE and BuChE inhibitors;    molecular docking;    MM-GBSA;   

DOI  :  10.3390/molecules181012951

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.