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Synthesis of bistetrahydroquinolines as potential anticholinesterasic agents by double Diels-Alder reactions.

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.

SUBMITTER: Duarte Y

PROVIDER: S-EPMC6270290 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Synthesis of bistetrahydroquinolines as potential anticholinesterasic agents by double Diels-Alder reactions.

Duarte Yorley Y Gutiérrez Margarita M Astudillo Luis L Alzate-Morales Jans J Valdés Natalia N

Molecules (Basel, Switzerland) 20131017 10

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 (ACh ...[more]

PMID: 24141245

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